5874-57-7

Basic information

• Product Name: D-Serine methyl ester hydrochloride
• Synonyms: METHYL D-SERINATE HYDROCHLORIDE;H-D-SER-OME HCL;D-SERINE METHYL ESTER HYDROCHLORIDE;D-SERINE METHYL ESTER HYDROCHLORIDE SALT;D-SERINE-OME HCL;H-D-Ser-OMe.HCI;D-Ser-OMe.HCl;D-Serine Methyl Ester HCl
• CAS NO: 5874-57-7
• Molecular Formula: C₄H₉NO₃*ClH
• Molecular Weight: 155.58
• EINECS: 1533716-785-6
• Product Categories: Amino ACIDS SERIES;Amino Acids;Amino Acids and Derivatives;All Aliphatics;Amino hydrochloride;Aliphatics;Amino Acids & Derivatives;Amino Acid Derivatives;Peptide Synthesis;Serine
• Mol File: 5874-57-7.mol
• Article Data: 40

Chemical Properties

• Melting Point: 163-166 °C(lit.)
• Boiling Point: 234.7 °C at 760 mmHg
• Flash Point: 95.8 °C
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.62 g/cm³
• Vapor Pressure: 4.96E-15mmHg at 25°C
• Refractive Index: 1.693
• Storage Temp.: -15°C
• Solubility: Soluble in ethanol and methanol.
• CAS DataBase Reference: D-Serine methyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: D-Serine methyl ester hydrochloride(5874-57-7)
• EPA Substance Registry System: D-Serine methyl ester hydrochloride(5874-57-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 5874-57-7(Hazardous Substances Data)

Usage

Chemical Description

D-serine methyl ester hydrochloride is a starting material used in the synthesis.

Description

D-Serine methyl ester hydrochloride, with the CAS number 5874-57-7, is a white solid compound that is utilized in various organic synthesis processes. It is a derivative of D-Serine, an important amino acid involved in several biological processes, and features a methyl ester group attached to the hydrochloride salt.

Uses

Used in Organic Synthesis:
D-Serine methyl ester hydrochloride is used as a synthetic building block for the creation of various organic compounds. Its unique structure allows it to be a versatile reagent in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, D-Serine methyl ester hydrochloride is used as an intermediate in the development of drugs targeting the central nervous system. Its role in modulating the activity of N-methyl-D-aspartate (NMDA) receptors makes it a valuable compound for the treatment of neurological disorders such as schizophrenia, Alzheimer's disease, and other cognitive impairments.
Used in Research and Development:
D-Serine methyl ester hydrochloride is also employed as a research tool in the field of biochemistry and neuroscience. It helps researchers understand the role of D-Serine in various biological processes and its interaction with other molecules, contributing to the advancement of scientific knowledge in these areas.
Used in Analytical Chemistry:
As a white solid with distinct chemical properties, D-Serine methyl ester hydrochloride can be used in analytical chemistry for the development of new methods and techniques for the detection, quantification, and analysis of amino acids and their derivatives in various samples, including biological and environmental matrices.

InChI:InChI=1/C17H12N4OS/c18-10-12(17(19)22)9-13-11-21(14-5-2-1-3-6-14)20-16(13)15-7-4-8-23-15/h1-9,11H,(H2,19,22)/b12-9+

Synthetic route

methanol (67-56-1) + D-Serine (312-84-5) → R-(-)-serine methyl ester hydrochloride (5874-57-7)

Conditions	Yield
With acetyl chloride for 2.5h; Heating;	100%
Stage #1: methanol; D-Serine With acetyl chloride at 0℃; Stage #2: In methanol for 3h; Heating;	100%
With hydrogenchloride In water at 55℃;	100%

methanol (67-56-1) + D-Serine (312-84-5) + acetyl chloride (75-36-5) → R-(-)-serine methyl ester hydrochloride (5874-57-7)

Conditions	Yield
Stage #1: methanol; acetyl chloride for 0.0833333h; Cooling with ice; Stage #2: D-Serine for 2h; Reflux;	97%

D-Serine (312-84-5) + acetyl chloride (75-36-5) → R-(-)-serine methyl ester hydrochloride (5874-57-7)

Conditions	Yield
In methanol for 15.5h; Reflux;	91%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + benzyl chloroformate (501-53-1) → (R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate (93204-36-5)

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; Cooling with ice;	100%
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 12h;	91%
With sodium hydrogencarbonate	80%

di-tert-butyl dicarbonate (24424-99-5) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8)

Conditions	Yield
Stage #1: R-(-)-serine methyl ester hydrochloride With triethylamine In dichloromethane for 0.5h; Cooling with ice; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃; for 16.5h; Cooling with ice;	100%
With triethylamine In tetrahydrofuran at 0 - 140℃; for 0.333333h; Inert atmosphere; Microwave irradiation;	99%
With triethylamine In tetrahydrofuran at 0 - 50℃; for 17h; Inert atmosphere;	97%

bis(trichloromethyl) carbonate (32315-10-9) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → (R)-2-oxo-oxazolidine-4-carboxylic acid methyl ester (144542-43-8)

Conditions	Yield
In tetrahydrofuran for 4h; Heating;	100%
In tetrahydrofuran for 4h; Reflux; Inert atmosphere;	98%
In tetrahydrofuran at 0 - 80℃; for 2h;	75%

trityl chloride (76-83-5) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → (2R)-3-hydroxy-2-(tritylamino)propanoic acid methyl ester (116457-91-1)

Conditions	Yield
With triethylamine In chloroform at 0℃; for 1h;	99%
With triethylamine In 1,2-dichloro-ethane at 50℃; for 12h;	97%
With triethylamine In dichloromethane at 0 - 25℃; for 16h;	95%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + benzaldehyde (100-52-7) → methyl (2R)-2-(benzylamino)-3-hydroxypropanoate (123639-56-5, 131110-76-4, 144001-42-3)

Conditions	Yield
Stage #1: R-(-)-serine methyl ester hydrochloride; benzaldehyde With magnesium sulfate; triethylamine In dichloromethane at 20℃; for 24h; Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 3h; Further stages.;	99%
Stage #1: R-(-)-serine methyl ester hydrochloride With triethylamine In methanol at 0℃; for 0.25h; Inert atmosphere; Stage #2: benzaldehyde In methanol at 20℃; for 2h; Inert atmosphere; Stage #3: With sodium tetrahydroborate In methanol at 0℃; Inert atmosphere;	99%
Stage #1: R-(-)-serine methyl ester hydrochloride; benzaldehyde With triethylamine Stage #2: With sodium tetrahydroborate	79%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropionic acid methyl ester (874817-14-8)

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water cooling;	99%
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 4.33333h;	95%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + 2,2-Dimethylmalonyl chloride (5659-93-8) → N,N'-bis[(1R)-(1-methoxycarbonyl)-2-hydroxyethyl]-2,2-propanedicarboxamide

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃; Inert atmosphere;	99%

dimethoxyacetaldehyde (51673-84-8) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → (2R)-2-(2,2-dimethoxyethylamino)-3-hydroxypropionic acid methyl ester

Conditions	Yield
With hydrogen; triethylamine; palladium on activated charcoal In methanol; water at 20℃; for 16h;	98%
With palladium 10% on activated carbon; hydrogen; triethylamine In methanol; water at 20℃;

ethyl trifluoroacetate, (383-63-1) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → (R)-3-Hydroxy-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester (312-84-5)

Conditions	Yield
In methanol at 20℃; for 15h;	98%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + trifluoroacetic anhydride (407-25-0) → (R)-3-Hydroxy-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester (312-84-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 6h;	98%

tert-butyldicarbonate (34619-03-9) + R-(-)-serine methyl ester hydrochloride (5874-57-7) + tert-butylchlorodiphenylsilane (58479-61-1) → methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(tert-butyldiphenylsilyloxy)propanoate (171564-48-0)

Conditions	Yield
Stage #1: tert-butyldicarbonate; R-(-)-serine methyl ester hydrochloride With sodium hydrogencarbonate In tetrahydrofuran; water Stage #2: tert-butylchlorodiphenylsilane With 1H-imidazole In dichloromethane	98%

1-(benzyloxy)-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl 4-methylbenzenesulfonate (1613522-41-0) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → methyl (R)-2-((1-(benzyloxy)-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)amino)-3-hydroxypropanoate (1613522-64-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 1h;	97%

dehydroabietic acid (1740-19-8) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → methyl N-(abiet-8,11,13-trien-18-yl)-D-serinate

Conditions	Yield
Stage #1: dehydroabietic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: R-(-)-serine methyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 20℃; for 1h;	97%

carbon monoxide (201230-82-2) + R-(-)-serine methyl ester hydrochloride (5874-57-7) + (1R)-2-iodo-1,7,7-trimethylbicyclo<2.2.1>hept-2-ene (22885-95-6) → C15H23NO4

Conditions	Yield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; for 1h; diastereoselective reaction;	96%

benzyl bromide (100-39-0) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → (R)-methyl 2-(dibenzylamino)-3-hydroxypropanoate (202478-34-0)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 24h; Alkylation;	95%
With sodium hydrogencarbonate; sodium iodide In tetrahydrofuran; dimethyl sulfoxide for 2h; Heating;	92%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 5h;	91.7%

Divinyl sulfone (77-77-0) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → methyl (R)-2-(1,1-dioxidothiomorpholino)-3-hydroxy propanoate

Conditions	Yield
With ethanol; triethylamine In 1,4-dioxane at 85℃; for 3h;	95%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → C18H26N2O6

Conditions	Yield
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃;	95%

carbon monoxide (201230-82-2) + R-(-)-serine methyl ester hydrochloride (5874-57-7) + (1S,4S)-2-iodobornene → C15H23NO4

Conditions	Yield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; for 1h; diastereoselective reaction;	95%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + JP-7 (170787-77-6) → (R)-2-[(1-{4-[(3,5-Dimethyl-phenylcarbamoyl)-methyl]-phenoxy}-cyclopentanecarbonyl)-amino]-3-hydroxy-propionic acid methyl ester (328236-00-6)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;	94.7%

5-bromo-2-methoxybenzoyl chloride (62910-63-8) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → (R)-2-(5-Bromo-2-methoxy-benzoylamino)-3-hydroxy-propionic acid methyl ester (380223-64-3)

Conditions	Yield
Stage #1: R-(-)-serine methyl ester hydrochloride With triethylamine In chloroform at -5℃; for 0.0833333h; Stage #2: 5-bromo-2-methoxybenzoyl chloride With triethylamine In chloroform at 0 - 20℃; for 0.25h;	94%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + acetyl chloride (75-36-5) → (R)-methyl 2-acetamido-3-hydroxypropionate

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere;	94%
With triethylamine In dichloromethane at -10 - 5℃; for 3h;	90%
With triethylamine In dichloromethane at -10 - 0℃; for 3h; Green chemistry;	90%

t-butylglyoxal (4480-47-1) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → methyl (R)-2-tert-butyloxazolidine-4-carboxylate (257291-68-2)

Conditions	Yield
With triethylamine In pentane at 55℃; for 72h; Dean Stark conditions; optical yield given as %de;	94%

C25H24N8O8S + R-(-)-serine methyl ester hydrochloride (5874-57-7) → C29H31N9O10S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 1h;	94%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + Fmoc-Thr-OH (73731-37-0) → (R)-2-[(2S,3R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-hydroxy-propionic acid methyl ester (609359-05-9)

Conditions	Yield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 25℃; for 3h;	93%
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃; for 2h;	70%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + benzoyl chloride (98-88-4) → N-benzoyl-D-serine methyl ester (1040384-28-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	92%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 2h;	92%
With triethylamine In methanol at 0℃;

(S)-2-[{(allyloxy)carbonyl}amino]-4-methylpentanoic acid (98204-51-4) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → N-(N-(prop-2-enyloxycarbonyl)-L-leucyl)-D-serine methyl ester

Conditions	Yield
Stage #1: (S)-2-[{(allyloxy)carbonyl}amino]-4-methylpentanoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1h; Stage #2: R-(-)-serine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 48h;	92%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + benzimidic acid ethyl ester (825-60-5) → (R)-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (105308-52-9)

Conditions	Yield
In 1,2-dichloro-ethane	91.4%
In dichloromethane; water for 24h; Ambient temperature;	75.3%
In 1,2-dichloro-ethane for 20h; Heating / reflux;

R-(-)-serine methyl ester hydrochloride (5874-57-7) + 2-naphthaloyl chloride (2243-83-6) → N-(2-naphthoyl)-D-serine methyl ester (1312671-66-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 2h;	91%

Upstream product

• 67-56-1 methanol 
• 312-84-5 D-Serine 
• 75-36-5 acetyl chloride 

Downstream Products

• 6062-60-8 N-(N-Benzloxycarbonyl-D-seryl)-D-serin-methylester 
• 6129-17-5 N-(N-Benzloxycarbonyl-L-seryl)-D-serin-methylester 
• 155225-25-5 N--(R)-serine methylester 
• 102683-26-1 N-(benzyloxycarbonyl)-L-tyrosyl-D-serine methyl ester 
• 145401-83-8 (R)-α-methylbenzylcarbamoyl-D-serine methyl ester 
• 116457-91-1 (2R)-3-hydroxy-2-(tritylamino)propanoic acid methyl ester 
• 155225-24-4 N--(R)-serine methylester 
• 123639-56-5 methyl (2R)-2-(benzylamino)-3-hydroxypropanoate 
• 105308-52-9 (R)-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 97102-78-8 N(Im),N'(α)-ditrityl-L-histidyl-D-serine methyl ester 
• 161644-41-3 N-(phenylthioacetyl)-D-serine methyl ester 
• 17460-66-1 Carbobenzoxy-Leu-D-Ser 
• 17460-58-1 (2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-hydroxypropanoic acid 
• 17460-71-8 Carbobenzoxy-D-Val-D-Ser 

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