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[ CAS No. 1263045-16-4 ] {[proInfo.proName]}

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Chemical Structure| 1263045-16-4
Chemical Structure| 1263045-16-4
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Product Details of [ 1263045-16-4 ]

CAS No. :1263045-16-4 MDL No. :MFCD13184954
Formula : C18H28N2O9 Boiling Point : No data available
Linear Structure Formula :- InChI Key :IAJVEYLYYHOZEY-UHFFFAOYSA-N
M.W : 416.42 Pubchem ID :51340949
Synonyms :
Chemical Name :1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-oxo-7,10,13,16-tetraoxa-4-azanonadecan-19-oic acid

Safety of [ 1263045-16-4 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1263045-16-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1263045-16-4 ]

[ 1263045-16-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 1343407-40-8 ]
  • [ 1263045-16-4 ]
  • [ 1343407-44-2 ]
YieldReaction ConditionsOperation in experiment
50% With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃; Amine 10 (99 mg, 0.109 mmol, 1 eq) was added to a solution of NHS-PEG4-Maleimide (Thermo Scientific, 61.6 mg, 0.120 mmol, 1.1 eq) and TEA (18.2 μL, 0.130 mmol, 1.2 eq) in a mixture of anhydrous DCM (5 mL) and DMF (1 mL). The reaction was allowed to stir at room temperature overnight at which point it was found to be almost complete by LC/MS (3.27 min (ES+) m/z (relative intensity) 1307.55 ([M+H]+., 100)). The volatiles were removed by evaporation under reduced pressure. The residue was purified by flash chromatography (gradient from 3/97 up to 5/95 methanol/chloroform) to yield 71 mg (50%) of pure product 13.[0440]Analytical Data: 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 7.50 (d, 2H, J=8.47 Hz), 7.28 (s, 1H), 7.25-7.20 (m, 2H), 7.18-7.01 (m, 9H), 6.89 (d, 1H, J=7.58 Hz), 6.79 (d, 2H, J=8.68 Hz), 6.59 (s, 2H), 6.51 (s, 1H), 5.77 (d, 1H, J=6.42 Hz), 5.25 (d, 1H, J=11.43 Hz), 4.83-4.64 (m, 2H), 4.63-4.49 (m, 1H), 4.43-4.38 (m, 1H), 4.18 (s, 1H), 3.96-3.85 (m, 1H), 3.84 (s, 3H), 3.76-3.56 (m, 9H), 3.57-3.34 (m, 15H), 3.34-3.20 (m, 3H), 3.15 (dd, 1H, J=14.22 Hz, J=5.60 Hz), 3.07-2.89 (m, 4H), 2.48-2.29 (m, 4H), 1.97-1.90 (m, 1H), 1.61-1.39 (m, 3H), 1.35 (s, 9H), 1.29-1.12 (m, 4H). MS (ES+) m/z (relative intensity) 1307.55 ([M+H]+., 100).
  • 2
  • [ 756525-91-4 ]
  • [ 1263045-16-4 ]
  • 3
  • [ 55750-62-4 ]
  • [ 1615234-93-9 ]
  • [ 1263045-16-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-blc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
0.227g With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; [0277] Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
  • 4
  • [ 6066-82-6 ]
  • [ 1263045-16-4 ]
  • [ 756525-99-2 ]
YieldReaction ConditionsOperation in experiment
0.109 g With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-blc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
0.109 g With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Synthesis of linker-drugReferring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
0.109g With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; [0277] Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
330 mg With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2h; The product 4-11 (1.0 g, 2.4 mmol) obtained in the previous step and EDC-HCl (0.55 g, 2.88 mmol) were dissolved in 25 mL DCM, HOSu (0.33 g, 2.88 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. 50 mL water was added, the mixture was then extracted with EtOAc for 3 times (50 mL×3). The organic phases were combined, washed with saturated brine for 3 times (50 mL×3), dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by prep-HPLC to give 330 mg product as colorless oil, yield 27%. LCMS (ESI) m/z 514.2 (M+H)+.

  • 5
  • [ 1263045-16-4 ]
  • (11S,11aS,11'S,11a'S)-di-tert-butyl 8,8'-(((5-(3-aminoprop-1-yn-1-yl)-1,3-phenylene)bis(methylene))bis(oxy))bis(7-methoxy-2-methylene-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate) [ No CAS ]
  • (11S,11aS,11'S,11a'S)-di-tert-butyl 8,8′-(((5-(1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,19-dioxo-7,10,13,16-tetraoxa-4,20-diazatricos-22-yn-23-yl)-1,3-phenylene)bis(methylene))bis(oxy))bis(7-methoxy-2-methylene-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
67 mg With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h;Inert atmosphere; (b) (11S,11aS,11'S,11a'S)-di-tert-butyl 8,8'-(((5-(1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,19-dioxo-7,10,13,16-tetraoxa-4,20-diazatricos-22-yn-23-yl)-1,3-phenylene)bis(methylene))bis(oxy))bis(7-methoxy-2-methylene-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate) (9) <strong>[1263045-16-4]MAL-dPEG4-acid</strong> (88 mg, 0.21 mmol) was added to a stirred solution of EDCI (41 mg, 0.21 mmol) and the crude primary amine 8 in dry DCM (4 mL) at room temperature. The reaction mixture was stirred under an argon atmosphere for 3 hours at which point analysis by LC/MS showed a substantial amount of desired product at retention time 3.58 min (ES+) m/z 1475 ([M+H]+, ?10% relative intensity), 1498 ([M+Na]+, ?5% relative intensity) accompanied by a side product at retention time 3.85 min. The reaction mixture was diluted with DCM (30 mL) and washed with H2O (3*10 mL), brine (20 mL), dried (MgSO4), filtered and evaporated in vacuo to provide the crude product. Purification by flash chromatography (gradient elution: 100% DCM to 96:4 v/v DCM/MeOH) gave the maleimide 9 as a foam (67 mg, 22% yield over 2 steps).
67 mg With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h;Inert atmosphere; <strong>[1263045-16-4]MAL-dPEG4-acid</strong> (88 mg, 0.21 mmol) was added to a stirred solution of EDCI (41 mg, 0.21 mmol) and the crude primary amine 8 in dry DCM (4 mL) at room temperature. The reaction mixture was stirred under an argon atmosphere for 3 hours at which point analysis by LC/MS showed a substantial amount of desired product at retention time 3.58 min (ES+) mlz 1475 ([M+ H]+ , -10% relative intensity), 1498 ([M+ Na]+', -5% relative intensity) accompanied by a side product at retention time 3.85 min. The reaction mixture was diluted with DCM (30 mL) and washed with H20 (3 x 10 mL), brine (20 mL), dried (MgS04), filtered and evaporated in vacuo to provide the crude product. Purification by flash chromatography (gradient elution: 100% DCM to 96:4 v/v DCM/MeOH) gave the maleimide 9 as a foam (67 m 22% yield over 2 steps).
  • 6
  • [ 1263045-16-4 ]
  • (11aS,11a'S)-8,8'-(((5-(4-(3-aminopropyl)piperazin-1-yl)-1,3-phenylene)bis(methylene))bis(oxy))bis(7-methoxy-2-methylene-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-5(11aH)-one) [ No CAS ]
  • N-(3-(4-(3,5-bis((((S)-7-methoxy-2-methylene-5-oxo-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)methyl)phenyl)piperazin-1-yl)propyl)-1-(3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido)-3,6,9,12-tetraoxapentadecan-15-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46 mg With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h;Inert atmosphere; (c) N-(3-(4-(3,5-bis((((S)-7-methoxy-2-methylene-5-oxo-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)methyl)phenyl)piperazin-1-yl)propyl)-1-(3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido)-3,6,9,12-tetraoxapentadecan-15-amide (13) <strong>[1263045-16-4]MAL-dPEG4-acid</strong> (42 mg, 0.10 mmol) was added to a stirred solution of EDCI (20 mg, 0.10 mmol) and the crude primary amine 12 (77 mg, 0.10 mmol) in dry DCM (4 mL) at room temperature. The reaction mixture was stirred under an argon atmosphere for 3 hours at which point analysis by LC/MS showed complete consumption of starting material, a substantial amount of desired product at retention time 2.42 min (ES+) m/z 1176 ([M+H2O]+, ?5% relative intensity) and excess <strong>[1263045-16-4]MAL-dPEG4-acid</strong> at retention time 2.05 min (weak signal on diode array but detectable on ES+/ES-). The reaction mixture was diluted with DCM (30 mL) and washed with H2O (15 mL), brine (20 mL), dried (MgSO4), filtered and evaporated in vacuo to provide the crude product. Purification by flash chromatography (gradient elution: 100% CHCl3 to 93:7 v/v CHCl3/MeOH) gave the maleimide 13 as a foam (46 mg, 55%). Note that trace amounts of excess <strong>[1263045-16-4]MAL-dPEG4-acid</strong> could not be removed using flash chromatography.
  • 7
  • [ 1263045-16-4 ]
  • (11aS,11a'S)-8,8'-(((5-(piperazin-1-yl)-1,3-phenylene)bis(methylene))bis(oxy))bis(7-methoxy-2-methylene-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]-benzodiazepin-5(11aH)-one) [ No CAS ]
  • N-(15-(4-(3,5-bis((((S)-7-methoxy-2-methylene-5-oxo-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)methyl)phenyl)piperazin-1-yl)-15-oxo-3,6,9,12-tetraoxapentadecyl)-3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2h;Inert atmosphere; (c) N-(15-(4-(3,5-bis((((S)-7-methoxy-2-methylene-5-oxo-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)methyl)phenyl)piperazin-1-yl)-15-oxo-3,6,9,12-tetraoxapentadecyl)-3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamide (17) N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (35 mg, 0.18 mmol, 1.1 eq) was added to a solution of compound (15) (116 mg, 0.165 mmol, 1.0 eq) and <strong>[1263045-16-4]1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-oxo-7,10,13,16-tetraoxa-4-azanonadecan-19-oic acid</strong> (16) (69 mg, 0.165 mmol, 1.0 eq) in anhydrous DCM (5 mL) under Argon. The resultant solution was stirred at room temperature for 2 h. The reaction mixture was diluted with DCM (50 mL), washed with water (100 mL), saturated sodium hydrogen carbonate solution (100 mL), water (100 mL), brine (100 mL), dried (MgSO4) and evaporated under reduced pressure. Purification by flash column chromatography [CHCl3/MeOH 0% to 5% in 1% increments] gave the product 17 as a yellow glass (0.058 g, 32%) Analytical Data: [α]18D=[+628] (c=0.25, CHCl3); RT 2.65 min; MS (ES+) m/z (relative intensity) 1101 ([M+1]+, 40)
  • 8
  • [ 55750-62-4 ]
  • [ 756525-91-4 ]
  • [ 1263045-16-4 ]
YieldReaction ConditionsOperation in experiment
0.227 g Synthesis of linker-drugReferring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
  • 9
  • [ 7423-55-4 ]
  • [ 1263045-16-4 ]
  • 10
  • (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-sulfopropanoic acid [ No CAS ]
  • [ 260367-12-2 ]
  • [ 1263045-16-4 ]
  • (R)-28-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-7,10,26-trioxo-8-(sulfomethyl)-3,13,16,19,22-pentaoxa-6,9,25-triazaoctacosan-1-oic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
The title compound was synthesized using solid phase peptide synthesis as described herein. 2-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethoxy)acetic acid (1543 mg) was dissolved in 10 mL dioxane, and the solvent was concentrated under reduced pressure. (The procedure was repeated twice). The material was lyophilized overnight. The dioxane-dried amino acid was dissolved in 20 mL sieve-dried dichloromethane to which was added N,N- diisopropylethylamine (4.07 mL). The solution was added to a 2-chlorotrityl solid support resin (8000 mg), which was previously washed (twice) with sieve-dried dichloromethane. The mixture of resin and amino acid was shaken at ambient temperature for 4 hours, drained, washed with 17:2: 1 dichloromethane:methanol:N,N-diisopropylethylamine, and washed three times with N,N- dimethylformamide. The mixture was then washed three more times, alternating between sieve-dried dichloromethane and methanol. The loaded resin was dried in a vacuum oven at 40 C. The resin loading was determined by quantitative Fmoc-loading test measuring absorbance at 301 nm of a solution obtained by deprotecting a known amount of resin by treatment with 20% piperidine in N,N- dimethylformamide. All Fmoc deprotection steps were performed by treatment of the resin with 20% piperidine in N,N-dimethylformamide for 20 minutes followed by a washing step with N,N- dimethylformamide. Coupling of the amino acids (R)-2-((((9H-fluoren-9- yl)methoxy)carbonyl)amino)-3-sulfopropanoic acid and subsequently l-(2,5-dioxo-2,5-dihydro-lH- pyrrol-l-yl)-3 -oxo-7, 10, 13, 16-tetraoxa-4-azanonadecan-19-oic acid was done by activation of 4 equivalents of amino acid with 4 equivalents of ((lH-benzo[d][l,2,3]triazol-l-yl)oxy)tri(pyrrolidin-l- yl)phosphonium hexafluorophosphate(V) and 8 equivalents of N,N-diidopropylethylamine in N,N- dimethylformamide for one minute followed by incubation with the resin for one hour. The title compound was cleaved from the resin by treatment with 5 % trifluoroacetic acid in dichloromethane for 30 minutes. The resin was filtered, and the filtrate was concentrated under reduced pressure to yield the title compound which was used in the next step without further purification. MS (ESI) m/e 669.0 (M+H)+
The title compound was synthesized using solid phase peptide synthesis as described herein. 2-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethoxy)acetic acid (1543 mg) was dissolved in 10 mLdioxane, and the solvent was concentrated under reduced pressure. (The procedure was repeated twice). The material was lyophilized overnight. The dioxane-dried amino acid was dissolved in 20 mL sieve-dried dichloromethane to which was added N,N-diisopropylethylamine (4.07 mL). The solution was added to a 2-chlorotrityl solid support resin (8000 mg), which was previously washed(twice) with sieve-dried dichloromethane. The mixture of resin and amino acid was shaken at ambient temperature for 4 hours, drained, washed with 17:2:1 dichloromethane:methanol:N,Ndiisopropylethylamine, and washed three times with N,N-dimethylformamide. The mixture was then washed three more times, alternating between sieve-dried dichloromethane and methanol. The loaded resin was dried in a vacuum oven at 40 C. The resin loading was determined by quantitative Fmoc20 loading test measuring absorbance at 301 nm of a solution obtained by deprotecting a known amountof resin by treatment with 20% piperidine in N,N-dimethylformamide. All Fmoc deprotection steps were performed by treatment of the resin with 20% piperidine in N,N-dimethylformamide for 20 minutes followed by a washing step with N,N-dimethylformamide. Coupling of the amino acids (R)2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-sulfopropanoic acid and subsequently 1 -(2,5-dioxo-2,5-dihydro- 1 H-pyrrol- 1 -yl)-3 -oxo-7, 10,13,1 6-tetraoxa-4-azanonadecan- 19-oic acid was done by activation of 4 equivalents of amino acid with 4 equivalents of ((1H-benzo[d][1,2,3]triazol-1- yl)oxy)tri(pyrrolidin- 1 -yl)phosphonium hexafluorophosphate(V) and 8 equivalents of N,Ndiidopropylethylamine in N,N-dimethylformamide for one minute followed by incubation with the resin for one hour. The title compound was cleaved from the resin by treatment with 5 %trifluoroacetic acid in dichloromethane for 30 minutes. The resin was filtered, and the filtrate was concentrated under reduced pressure to yield the title compound which was used in the next step without further purification. MS (ESI) m/e 669.0 (M+H).
The title compound was synthesized using solid phase peptide synthesis as described herein. 2-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethoxy)acetic acid (1543 mg) was dissolved in 10 mL dioxane, and the solvent was concentrated under reduced pressure. (The procedure was repeated twice). The material was lyophilized overnight. The dioxane-dried amino acid was dissolved in 20 mL sieve-dried dichloromethane to which was added N,N-diisopropylethylamine (4.07 mL). The solution was added to a 2-chlorotrityl solid support resin (8000 mg), which was previously washed (twice) with sieve-dried dichloromethane. The mixture of resin and amino acid was shaken at ambient temperature for 4 hours, drained, washed with 17:2:1 dichloromethane:methanol:N,N-diisopropylethylamine, and washed three times with N,N-dimethylformamide. The mixture was then washed three more times, alternating between sieve-dried dichloromethane and methanol. The loaded resin was dried in a vacuum oven at 40 C. The resin loading was determined by quantitative Fmoc-loading test measuring absorbance at 301 nm of a solution obtained by deprotecting a known amount of resin by treatment with 20% piperidine in N,N-dimethylformamide. All Fmoc deprotection steps were performed by treatment of the resin with 20% piperidine in N,N-dimethylformamide for 20 minutes followed by a washing step with N,N-dimethylformamide. Coupling of the amino acids (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-sulfopropanoic acid and subsequently <strong>[1263045-16-4]1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-oxo-7,10,13,16-tetraoxa-4-azanonadecan-19-oic acid</strong> was done by activation of 4 equivalents of amino acid with 4 equivalents of ((1H-benzo[d][1,2,3]triazol-1-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) and 8 equivalents of N,N-diidopropylethylamine in N,N-dimethylformamide for one minute followed by incubation with the resin for one hour. The title compound was cleaved from the resin by treatment with 5% trifluoroacetic acid in dichloromethane for 30 minutes. The resin was filtered, and the filtrate was concentrated under reduced pressure to yield the title compound which was used in the next step without further purification. MS (ESI) m/e 669.0 (M+H)+.
  • 11
  • [ 1263045-16-4 ]
  • (11S,11aS,11'S,11a'S)-di-tert-butyl 8,8'-(((5-(3-aminopropa-1-yne-1-yl)-1,3 phenylene)bis(methylene))bis(oxy))bis(7-methoxy-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-10(5H)carboxylate) [ No CAS ]
  • (11S,11aS,11'S,11a'S)-di-tert-butyl 8,8'-(((5-(1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,19-dioxo-7,10,13,16-tetraoxa-4,20-diazatricos-22-yn-23-yl)-1,3-phenylene)bis(methylene))bis(oxy))bis(7-methoxy-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-10(5H)carboxylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
80 mg With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h;Inert atmosphere; MAL-dPEG (registered trademark) 4-acid (37 mg, 0.089mmol) which, added to the DCM (4 ml) anhyride soln. stirring at room temperature in a second (17 mg, 0.089mmol) EDCI and roughness of a tertiary amine 1 8. The reaction mixture is stirred for 3 hours in an argon atmosphere, at this point of time by the analysis by LC/MS (method C), holding time by 1.69 (ES+) m/z 1450.55 ([M+H] +., about 10% relative intensity), 1498 ([M+Na] +., relative strength of about 80%) by, substantial amounts of the desired product is shown. The reaction mixture is diluted with DCM (30 ml), H 2 O (3×10mL), saline (20 ml) by washing, dehydrating (MgSO 4), by filtration, the crude product is evaporated in a vacuum. flash chromatography purified (gradient elution: from 100% DCM 96:4 vol./ vol. DCM/MeOH) by, a bubble obtd. alkylmaleimide 9 (80 mg, 2 at step 62% yield).
  • 12
  • [ 1263045-16-4 ]
  • (11aS,11a'S)-8,8'-(((5-(piperazin-1-yl)-1,3-phenylene)bis(methylene))bis(oxy))bis(7-methoxy 2,3-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(11aH)one) [ No CAS ]
  • N-(15-(4-(3,5-bis((((S)-7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)methyl)phenyl)piperazin-1-yl)-15-oxo-3,6,9,12-tetraoxapentadecyl)-3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.7 mg With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h;Inert atmosphere; MAL-dPEG (registered trademark) 4-acid (35 mg, 0.084mmol) which, added to the DCM (3 ml) anhyride soln. stirring at room temperature in a first (16 mg, 0.084mmol) EDCI and roughness of a tertiary amine 1 12. The reaction mixture is stirred for 3 hours in an argon atmosphere, at this point of time by the analysis by LC/MS (method C), dividing the holding time 1.24 (ES+) m/z 1077.40 ([M+H] +., 90% relative intensity) by, a substantial amount of the desired product is shown. The reaction mixture is diluted with DCM (30 ml), H 2 O (3×10mL), saline (20 ml) by washing, dehydrating (MgSO 4), by filtration, the crude product is evaporated in a vacuum. Preparative UPLC purified (gradient elution: 11 min. 87:13 vol./ vol. H 2 O/CH 3 CN over from 15:75 vol./ vol. H 2 O/CH 3 CN) by, a final product 13, obtained as a thin brown oil (4.7 mg, 5% yield at the step 2).
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