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[ CAS No. 192725-45-4 ] {[proInfo.proName]}

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Chemical Structure| 192725-45-4
Chemical Structure| 192725-45-4
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CAS No. :192725-45-4 MDL No. :MFCD09835123
Formula : C33H42N2O5 Boiling Point : No data available
Linear Structure Formula :- InChI Key :QYYDVAZZRBOAFD-AWCRTANDSA-N
M.W : 546.70 Pubchem ID :45039081
Synonyms :

Safety of [ 192725-45-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 192725-45-4 ]

* 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 [ 192725-45-4 ]

[ 192725-45-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 13335-71-2 ]
  • [ 144163-85-9 ]
  • [ 192725-45-4 ]
YieldReaction ConditionsOperation in experiment
76.7% With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 16h; [00289] Example 18. Preparation of tert-butyl ( 1 S,3S,4S> 1 -benzyl-4- { [(2,6-dimethy.phenoxy)acetyl] amino} -S-hydroxy-5-phenylpentylcarbamate; [00290] A solution of /erf-butyl (lS,3S,4ιS)-l-benzyI-3-hydroxy-5-phenyl-4-amino-pentylcarbamate (38.5 mg, 0.1 mmol), (2,6-dimethyl-phenoxy)-acetic acid (18.9 mg, 1.05 equivalents), l-(3-dimethyl aminopropyl)-3-ethylcarbodiimide hydrochloride (29.7 mg, 1.5 equivalents), and 1-hydroxybenzotriazole (20.4 mg, 1.5 equivalents) in N,N-dimethylformamide (1 mL) was stirred for 4 minutes at room temperature. To this mixture was added N-methylmorpholine (27.5 μL, 2.5 equivalents) and the solution was stirred for 16 hours. The reaction mixture was quenched with saturated sodium bicarbonate, extracted with EtOAc, washed with 10% citric acid, dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica (3% MeOH/ CH2CI2) gave a white solid (240 mg, 76.7%). IH NMR (300 MHz, DMSO-D6) δ ppm 1.31 (s, 9 H), 1.39 - 1.55 (m, J=6.99 Hz, 2 H), 2.14 (s, 6 H), 2.61 (d, ./=6.99 Hz, 2 H), 2.80 (d, 7=7.35 Hz, 2 H), 3.61 - 3.70 (m, 1 H), 3.84 (m, 1 H), 4.00 - 4.11 (m, 2 H), 4.20 - 4.38 (m, 1 H), 4.99 (d, 1 H), 6.66 (d, ./=9.19 Hz, 1 H), 6.88 - 7.28 (m, 13 H), 7.43 (d, 7=9.56 Hz, 1 H); MS m/z 547.4 (M+H)+.
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 10h; General procedure: To the mixture of compound 16 and the phenol relatedacetic acid derivative in DMF was added TBTU and Et3N,and stirred at room temperature for 10 hours. After evaporationof the solvent, the residue was purified on silica gel columnto afford 18, or 19, or 20 in 50-70% yield. By usingsimilar procedure, compounds 15 and 17 were converted into the amides 21 and 22. Products 18, 19, 20, 21 and 22 wereconfirmed by LCMS. Then compounds 21 or 22 were treatedby TFA/CH2Cl2 (9:1) for 30 min. After removal of the solventby co-evaporation with toluene, the residue was treatedwith N-phenylsulfonyl-valine in dry DMF in the presence ofTBTU and Et3N for 10 hours at room temperature under nitrogen.The volatiles of the reaction mixture were evaporatedand the residue was diluted with aqueous NaHCO3 and extractedwith CH2Cl2. Then the combined extracts wereevaporated and the residue was dissolved into ether and precipitatedwith hexane and filtered. The precipitated solidswere then dissolved into a mixture of CH2Cl2/MeOH, andmixed with a minimum amount of silica gel. After evaporatingthe volatiles, the silica gel adsorbed with the compoundswas loaded onto a silica gel column, and was washed withdichloromethane/ethyl acetate (3:1), then using methanol towash the column. The methanol fraction was concentrated,and the residue was suspended in hexane/ethyl acetate (1:1)and the solid product was filtered and washed with the samemixture to obtain the desired products 3, 4, 5, 23a, 23b and23c in more than 90% purities based on LCMS analysis.
With 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 10h; (9) Add compound 17 and an equimolar amount of 2,6-dimethylphenol acetic acid to tetramethylurea tetrafluoroborate (TBTU), triethylamine (Et3N) and dimethylformamide (DMF) Stir at room temperature for 10 hours to obtain compound 22 respectively. Compound 22 was subjected to acidic conditions to remove the Boc group, 15 mg of compound 22 was dissolved in 9:1 trifluoroacetic acid: H2O, stirred at room temperature for 30 minutes, and toluene was added After evaporation to dryness, the obtained residue was coupled with N-benzenesulfonylvaline in a mixed solvent of tetramethylurea tetrafluoroborate, triethylamine and dimethylformamide to obtain compound 5, which was confirmed by LCMS The resulting compound 5 is the structure.
30 g Add 14.2g (78.8mmol, purity>98%) 2,6-dimethylphenoxyacetic acid and 50mL ethyl acetate into a 250mL three-necked flask, stir to dissolve at room temperature,At room temperature, 12.2g (102mmol) of SOCl2 and 3 drops of DMF solution were added dropwise from a constant pressure dropping funnel (after 15min), and the temperature was raised to 50C for 4h.Then, after the solvent ethyl acetate was distilled off under reduced pressure, 60 mL of ethyl acetate was added to dissolve it for use.Add 26.2g (68mmol) of compound BDH into a 1L three-necked flask,300 mL ethyl acetate, 300 mL water and 31 g sodium bicarbonate solid were stirred at room temperature.After the solids are dissolved, add dropwise the ethyl acetate solution of the above acid chloride to the two-phase solution with vigorous stirring (after 15 minutes), and react at room temperature for 5 hours.HPLC monitors the raw material BDH after the reaction is complete. Separate the liquids, add 200 mL of 10% sodium bicarbonate aqueous solution to the organic phase,After stirring for 30 minutes at room temperature, the aqueous phase was separated and washed with 200 mL of water.Add 40 g of anhydrous sodium sulfate to the organic phase, dry, filter, concentrate, and vacuum dry to obtain 30 g of white solid.

  • 2
  • [ 192725-45-4 ]
  • [ 192725-49-8 ]
YieldReaction ConditionsOperation in experiment
100% N. (2S,3S,5S)-2-(2,6-Dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane To 4.5 g of the compound from Example 1I was added 40 ml each of CH2 Cl2 and trifluoroacetic acid. The solution was left at RT for 1 h. Concentration of the solution in vacuo provided the desired compound (100%). 300 MHz 1 H NMR (CDCl3) δ1.48 (m, 1H), 1.62 (m, 1H), 2.05 (m, 1H), 2.24 (s, 6H), 2.50 (m, 1H), 2.80 (m, 1H), 3.0-3.10 (m, 4H), 3.90 (d, J=10 Hz, 1H), 4.17 (m, 1H), 4.26 (ABq, J=13.5 Hz, 2H), 7.0 (m, 3H), 7.10 (m, 2H), 7.30 (m, 7H), 7.41 (d, J=10 Hz, 1H). Mass spectrum: (M+H)+ =447.
With trifluoroacetic acid; In dichloromethane; at 20℃; for 3.33333h; To a stirred solution of (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3- hydroxy-5-(t-butyloxycarbonylamino)-l,6-diphenylhexane (5.1 g) in methylene chloride (50 rnL) was added trifluoroacetic acid (10.65 g) at room temperature over a period of 20 minutes. The reaction mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and then water (100 mL) was added followed by methylene chloride (100 mL). To the cooled at about 10-15C biphasic mixture, solid sodium bicarbonate (12 g) was added portionwise, and finally its pH was adjusted to about 8.5 with aqueous sodium hydroxide. The organic layer was separated and washed with water (50 mL). Concentration of methylene chloride layer provided a residue as thick oil. Ethyl acetate (50 mL) was added into the above residue and stirred to yield a clear solution. To the stirred solution imidazole (2.1 g) was added at room temperature. The mixture was cooled to 00C. To the cold reaction mixture a suspension of acid chloride in dimethyl formamide (from step 1 of Example 5) was slowly added at about 0 to 50C during 30 minutes. The reaction mixture was stirred at 0 to 50C for next 30 minutes, then warmed to room temperature and stirred at room temperature for 12 hours. The reaction mixture was cooled down to 10C and quenched with aqueous hydrochloric acid (100 mL) at 10-150C. Ethyl acetate (50 mL) was added to the mixture and stirred at room temperature for 30 minutes. The organic layer was separated and washed with aqueous sodium bicarbonate (50 mL) followed by water (2 X 50 mL). Evaporation of the solvent under reduced pressure afforded crude material as an off-white solid which was dissolved in ethyl acetate (28 mL) at 45-5O0C and then heptane (28 mL) was slowly added at 50- 450C. The resulting clear solution was slowly allowed to cooled to room temperature and stirred at room temperature for 12 hours. A white solid, precipitated out from the solution was filtered and washed with 1:1 mixture of ethyl acetate and heptane (5 mL). The solid was dried under vacuum at 50-60C for 12 hours to yield the title compound as a white solid.Yield: 3.5 g
With trifluoroacetic acid; In dichloromethane; for 0.5h; General procedure: To the mixture of compound 16 and the phenol relatedacetic acid derivative in DMF was added TBTU and Et3N,and stirred at room temperature for 10 hours. After evaporationof the solvent, the residue was purified on silica gel columnto afford 18, or 19, or 20 in 50-70% yield. By usingsimilar procedure, compounds 15 and 17 were converted into the amides 21 and 22. Products 18, 19, 20, 21 and 22 wereconfirmed by LCMS. Then compounds 21 or 22 were treatedby TFA/CH2Cl2 (9:1) for 30 min. After removal of the solventby co-evaporation with toluene, the residue was treatedwith N-phenylsulfonyl-valine in dry DMF in the presence ofTBTU and Et3N for 10 hours at room temperature under nitrogen.The volatiles of the reaction mixture were evaporatedand the residue was diluted with aqueous NaHCO3 and extractedwith CH2Cl2. Then the combined extracts wereevaporated and the residue was dissolved into ether and precipitatedwith hexane and filtered. The precipitated solidswere then dissolved into a mixture of CH2Cl2/MeOH, andmixed with a minimum amount of silica gel. After evaporatingthe volatiles, the silica gel adsorbed with the compoundswas loaded onto a silica gel column, and was washed withdichloromethane/ethyl acetate (3:1), then using methanol towash the column. The methanol fraction was concentrated,and the residue was suspended in hexane/ethyl acetate (1:1)and the solid product was filtered and washed with the samemixture to obtain the desired products 3, 4, 5, 23a, 23b and23c in more than 90% purities based on LCMS analysis.
7.1 g With trifluoroacetic acid; In dichloromethane; at 0 - 25℃; for 0.00466667h;Inert atmosphere; Under the protection of nitrogen, 10.0g (18.3mmol) of the above white solid,After 100mL of dichloromethane is dissolved,20.8g (183mmol) of trifluoroacetic acid dissolved in 40mL of dichloromethane was added dropwise to the solution at 0-5C (after dripping in about 40min),This process needs to be added slowly to prevent side reactions.After the addition, the temperature was raised to 20-25C to react for 4 hours, and the reaction of the raw material intermediate 1 was monitored by HPLC to be complete. Vacuum distillation to recover unreacted trifluoroacetic acid,After evaporation to dryness, 200 mL of dichloromethane was added to dissolve, 200 mL of 10% NaHCO3 aqueous solution was washed to pH=8-9, and then the liquids were separated. Wash the organic phase again with 200 mL of water,Dry with anhydrous sodium sulfate, filter, and concentrate to obtain a pale yellow oil.Add 30mL of ethyl acetate/n-heptane (volume ratio 2:3) mixed solvent, and cool to 0,Stir and crystallize, filter, and vacuum dry at 40C to obtain 7.1g of white solid. Under nitrogen protection, 40mL of dry DMF, 1.1g (10.9mol) of dry triethylamine, 4.2g (9.1mmol) of this white solid, 2.0g (10mmol) ) Chiral acid, after 1.66g (12.3mmol) 1-hydroxybenzotriazole (HOBt),Stir at 0C for 20 minutes and then mix there,Add 2.1g (10.9mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC hydrochloride) in batches, raise it to 20-25 and react overnight (not low At 12h), HPLC monitored the reaction of Intermediate 2 to be complete. The DMF was evaporated under reduced pressure, 100mL ethyl acetate, 100mL 1.0mol/L dilute hydrochloric acid was added to wash, liquid separation, the organic phase was washed with 150mL 5wt% NaHCO3, 150mL distilled water, dried with anhydrous sodium sulfate and activated carbon decolorization, filtration and concentration A light yellow oily substance was obtained, crystallized with ethyl acetate and n-hexane 30g (ethyl acetate: n-hexane=1:1), filtered with suction, and dried at 40C to obtain a white solid, lopinavir, with a yield of 83 %, HPLC purity 99.76%.
With hydrogenchloride; In water; ethyl acetate; at 0 - 50℃; for 4h;Large scale; (2) Take 350.0 g of compound VI, put it in a three-necked flask, add 3.5 L of ethyl acetate, stir until the system is clear, after the solution is clear, cool to 0-5 oC and add 270ml of concentrated hydrochloric acid to the system. After the addition, the system was heated to 50 oC and reacted for 4 hours. TLC monitored the reaction to complete. Separate and collect the organic phase. Wash the aqueous phase with 2×700 ml ethyl acetate. After washing, separate and collect all the organic phases. The organic phase was saturated Wash with 1750 ml of brine, separate and collect the organic phase after washing, dry with anhydrous sodium sulfate for 2 h, filter with suction, spin dry the filtrate to obtain a pale yellow oily compound VII crude product for use.

  • 3
  • [ 192725-45-4 ]
  • (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane hydrochloride salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.1% With hydrogenchloride; In 1,4-dioxane; at 20℃; for 6h; [00291] Example 19. Preparation of 1,3-thiazol-5-ylmethyl(lS,3S,4S)-l-benzyl-4-[(2,6-dimethyl phenoxy)acetyl]amino}-3-hydroxy-5-phenylpentylcarbamate; <n="103"/>[00292] A solution of the compound of Example 18 (42 mg, 0.08 mmol) in 4N HCI/ dioxane (3 mL) was stirred at room temperature for 6 h. The reaction mixture was concentrated in vacuo, trituated with Et2O, and filtered to give a white solid (36 mg, 97.1%) which was used for the next step without further purification.
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