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[ CAS No. 5874-57-7 ] {[proInfo.proName]}

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Chemical Structure| 5874-57-7
Chemical Structure| 5874-57-7
Structure of 5874-57-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 5874-57-7 ]

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Product Details of [ 5874-57-7 ]

CAS No. :5874-57-7 MDL No. :MFCD00066121
Formula : C4H10ClNO3 Boiling Point : -
Linear Structure Formula :NH2CH(CH2OH)COOCH3·HCl InChI Key :NDBQJIBNNUJNHA-AENDTGMFSA-N
M.W : 155.58 Pubchem ID :11446470
Synonyms :
Chemical Name :H-D-Ser-OMe.HCl

Calculated chemistry of [ 5874-57-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 33.46
TPSA : 72.55 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.64
Log Po/w (WLOGP) : -0.72
Log Po/w (MLOGP) : -0.84
Log Po/w (SILICOS-IT) : -1.04
Consensus Log Po/w : -0.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.2
Solubility : 97.4 mg/ml ; 0.626 mol/l
Class : Very soluble
Log S (Ali) : -0.41
Solubility : 60.4 mg/ml ; 0.388 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.57
Solubility : 583.0 mg/ml ; 3.75 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 5874-57-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5874-57-7 ]

* 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 [ 5874-57-7 ]

[ 5874-57-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 76-83-5 ]
  • [ 5874-57-7 ]
  • [ 116457-91-1 ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine; In chloroform; at 0℃; for 1h; D-serine methyl ester hydrochloride (40 g, 0.26 mol) was dissolved in chloroform (360 mL). Triethylamine (90 mL, 0.64 mol) was added at 0 C. Slowly added triphenylchloromethane (72 g, 0.26 mol), reaction for 1 hour. Add chloroform (200 mL) at room temperature. Wash with water (500 mL), The organic phase is dried over anhydrous sodium sulfate. Concentrated by suction filtration, Get the title compound(93 g, yield 99%).
97% With triethylamine; In 1,2-dichloro-ethane; at 50℃; for 12h; Put (D)-serine methyl ester hydrochloride (10.0g, 64mmol, 1.0equiv.,) into a three-necked flask, dissolve it in 150mL 1,2-dichloroethane, and add triethylamine (16.0g, 2.5equiv.,) , And then add TrtCl (15.4g, 1.0 equiv.) in batches. Then the reaction system was placed in an oil bath at 50 C. and heated and stirred for 12 hours. TLC detected that the reactants disappeared completely, and the reaction system was placed in an ice-water bath. When the internal temperature reached 10C, a saturated aqueous ammonium chloride solution was slowly added dropwise to quench the reaction. The chloroform layer was separated, washed with saturated brine, dried with anhydrous sodium sulfate, filtered to obtain the organic phase, evaporated to remove the solvent, and recrystallized in a petroleum ether/ethyl acetate mixed solvent to obtain 22.38 g of white solid (compound A). The yield was 97%.
95% With triethylamine; In dichloromethane; at 0 - 25℃; for 16h; Methyl Trityl-D-Serinate To a stirred solution of methyl-D-serinate hydrochloride (2 g, 12.8 mmol) in DCM (10 mL) at 0 C., triethylamine (6.1 mL, 45.9 mmol) was added. Trityl chloride (4.26 g, 15.3 mmol) was then added and the reaction mixture was stirred for 16 hours at room temperature. After completion of the reaction (monitored by TLC), the reaction mixture was quenched with water (20 mL) and the aqueous layer was extracted with DCM (2*30 mL). The combined organic layer was washed with water (30 mL) and brine (30 mL) and dried over anhydrous Na2SO4. The organic part was filtered and concentrated under vacuum. The resulting crude material was purified by Isolera column chromatography (eluent: 27% EtOAc/PE; silica gel: 230-400 mesh) to afford the title compound. Yield: 95% (2.5 g, white solid). 1H NMR (400 MHz, DMSO-d6): δ 7.43 (d, J=8.0 Hz, 6H), 7.29 (t, J=8.0 Hz, 6H), 7.20 (t, J=7.2 Hz, 3H), 4.95-4.92 (m, 1H), 3.63-3.51 (m, 1H), 3.46-3.40 (m, 1H), 3.24-3.18 (m, 1H), 3.13 (s, 3H), 2.82-2.71 (m, 1H).
92% With triethylamine; In dichloromethane; at -5 - 20℃; A compound of D- serine methyl ester hydrochloride (1000g, 6.45mol, 1eq) was dissolved in 5L of dichloromethane, was added triethylamine (1955g, 19.35mol, 3eq), maintaining the temperature at -5 ~ 5 , min after the batch was added triphenylmethyl chloride (2152g, 7.74mol, 1.2eq) was stirred at room temperature until the reaction is complete, water was added quenched liquid separation, the organic phase was washed with hydrochloric acid, TLC testing to confirm no triethylamine dried over anhydrous sodium sulfate, the solvent was concentrated to give a white solid, a -D- N- trityl-serine methyl ester. Yield 92%.
With triethylamine; In dichloromethane; at 0℃; for 12h;Inert atmosphere; General procedure: To a suspension of (S)-serine methyl ester hydrochloride (0.50 g, 3.2 mmol) in DCM (7 ml) at 0 C, under a nitrogen atmosphere, was added dropwise triethylamine (1.0 ml, 7.1 mmol), followed by a solution of triphenylmethyl chloride (0.91 g, 3.2 mmol) in DCM (2 ml). After stirring at 0 C for 12 h the white precipitate was filtered and the filtrate was concentrated in vacuo to yield a white solid which was dissolved in ethyl acetate (10 ml), washed with 1 M aqueou NaHCO3 solution (10 ml), 10% aqueous citric acid solution (10 ml) and water (10 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo giving a white solid. Purification by flash column chromatography on silica gel in petroleum ether:ethyl acetate (4:1), gave N-trityl-(S)-serine methyl ester as a white solid (0.99 g, 86%).
With triethylamine; In dichloromethane; at 0℃; for 12h;Inert atmosphere; General procedure: N-Trityl-(S)-serine methylester. To a suspension of (S)-serine methyl ester hydrochloride (0.50 g, 3.2mmol) in DCM (7 ml) at 0 oC, under a nitrogen atmosphere, was added dropwise triethylamine (1.0 ml, 7.1 mmol), followed by a solution of triphenylmethyl chloride (0.91 g, 3.2 mmol) in DCM (2 ml). After stirring at 0 oC for 12 h the white precipitate was filtered and the filtrate was concentrated in vacuo to yield a white solid which was dissolved in ethyl acetate (10 ml), washed with 1 M aqueous NaHCO3 solution (10 ml), 10% aqueous citric acid solution (10 ml) and water (10 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo giving a white solid. Purification by flash column chromatography on silica gel in petroleum ether:ethyl acetate(4:1), gave N-trityl-(S)-serine methyl ester as a white solid (0.99 g, 86%).
With triethylamine; In chloroform; at 0 - 20℃; for 1h; Example 1: Preparation of (R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenvDbutanoyll- 3-(t-butoxymethyl)piperazin-2-one hydrochloride; Step 1: Preparation of (R)-methyl l-tritylaziridine-2-carboxylate; 200 g of D-serine methyl ester hydrochloride was added to 1.8 L of chloroform, and the reaction solution was cooled to 0C, to which 448 mL of triethylamine was then slowly added. 358.4 g of trityl chloride was slowly added to the reaction mixture which was then stirred for 1 hour. The reaction mixture was warmed to room temperature, and 1 L of chloroform was added thereto, followed by washing with 2.5 L of water. The organic layer was dried over magnesium sulfate and cooled to 0C, to which 484 mL of triethylamine and 15.7 g of 4- methylaminopyridine were then sequentially and slowly added. The reaction mixture was stirred for 5 min and 139 mL of methane sulfonyl chloride was slowly added thereto. The reaction mixture was warmed to room temperature, stirred for another 4 hours and then refluxed for 12 hours. The reaction mixture was cooled to room temperature, and washed with 4 L of water and then 3 L of brine. The organic layer was dried over magnesium sulfate and <n="17"/>concentrated to dryness under reduced pressure. 3 L of ethanol was added to the resulting residue which was then stirred. The resulting solids were filtered to afford 329 g of the title compound.IH NMR (400 MHz, CDC13): 7.42 to 7.49(m, 6H), 7.18 to 7.32(m, 9H), 7.68(s, IH),3.74(s, 3H), 2.24(m, IH), 1.87(m, IH), and 1.40(m, IH)
With triethylamine; In dichloromethane; at 0℃; for 24h;Inert atmosphere; (ft)-Methyl 3-Hydroxy-2-(λ/-tritylamino)propanoate (S. Bhatia and J. Hajdu, Tetrahedron Lett. 1998, 29, 31-34).; To a solution of D-serine methyl ester hydrochloride (20.00 g, 0.13 mol) and Et3N (35.82 mL, 0.26 mol) in CH2CI2 (80 mL) at 0 0C, was added in one portion a solution of TrCI (36.53 g, 0.13 mol) in CH2CI2 (80 mL). The mixture was allowed to stir at 0 0C (24 h) under Ar and then successively washed with 10% aqueous citric acid (120 mL) and saturated aqueous brine (120 mL). The organic layer was dried (Na2SO4) and evaporated in vacuo to yield 45.20 g (97%) of crude desired product as a pale yellow crystalline solid. The product was used for next step without further purification: Rf = 0.50 (1/1 EtOAc/hexanes); 1H NMR (CDCI3) δ 2.29 (br s, 1 H), 2.98 (br s, 1 H), 3.29 (S, OCH3), 3.51-3.60 (m, CHH'OH, CH), 3.64-3.74 (m, CHH'OH), 7.16-7.30 (m, 9 PhH), 7.47-7.50 (m, 6 PhH).

  • 2
  • [ 5874-57-7 ]
  • [ 100-52-7 ]
  • [ 123639-56-5 ]
YieldReaction ConditionsOperation in experiment
60% TEA (44.8 ml, 321.38 mmol) was added to a solution of methyl D-serinate hydrochloride (50 g, 321.38 mmol) and benzaldehyde (33 ml, 321.38 mmol) in methanol (250 ml) at 0C. The resulting suspension was stirred at room temperature for 2 hours. Then sodium borohydride (24 g, 634.39 mmol) was added slowly and the mixture stirred at room temperature for another 2 hours. The reaction mixture was quenched with water (200 ml), extracted with DCM (3 x 100 ml), the organic layer was dried over sodium sulphate, filtered and evaporated. The crude product was purified by flash silica chromatography, elution gradient 0 to 60% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford methyl N-benzyl-D-serinate (40 g, 60%) as a colourless oil. 1H NMR (400 MHz, CDCIs, 30C) 2.51 (2H, s), 3.48 (1H, dd), 3.65 (1H, dd), 3.76 - 3.84 (5H, m), 3.92 (1H, d), 7.36 (5H, m). m/z: ES+ [M+H]+ = 210.
The title compound was prepared according to literature (ref. JOC, 1990, 55(1 ), 111-122) starting from (D)-serine methyl ester hydrochloride (98%, from Aldrich) (D)-serine methyl ester hydrochloride (10g, 0.065 moles) was suspended in 50 ml of anhydrous methanol and cooled to 00C under nitrogen. Triethylamine (9 ml, 0.065 moles) was added dropwise, followed by benzaldehyde (6.6 ml, 0.065 moles). The reaction mixture was then warmed up and stirred at room temperature for 2 hours. Sodium borohydride (4.85g, 0.13 moles) were added in small portions over 2 hours. The resulting mixture was stirred at room temperature overnight. The mixture was then slowly added to 50 ml of HCI (20% solution) at 00C and the resulting solution was washed with diethyl ether (50 ml). The aqueous layer was then brought to basic pH by adding solid potassium carbonate and extracted with diethyl ether (3 x 50 ml). The combined organic extracts were dried (Na2SO4) and concentrated under vacuum to afford the title compound as colourless oil (10.95g). m/z = 210 [M+H]+
To (2R)-3-hydroxy-1-methoxy-1-oxopropan-2-aminium chloride (1 eq.) in MeOH (1.3 M) at 0C was added triethylamine (1 eq.). The reaction mixture was stirred for 10 minutes and benzaldehyde (1 eq) was added. The reaction mixture was stirred for 2 hours and NaBH4(1.5 eq.) was added portionwise to the reaction mixture over 30 mm. The reaction mixture was stirred at rt for 5hours and poured into a 1:1 mixture of saturated aqueous NH4C1 and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine and water, dried over Na2504, filtered and concentrated. The crude product was used as such for the next step.
  • 3
  • [ 5874-57-7 ]
  • [ 88038-94-2 ]
  • [ 1027426-91-0 ]
  • 4
  • [ 5874-57-7 ]
  • [ 115595-27-2 ]
  • [ 1026377-61-6 ]
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