112346-82-4

Basic information

• Product Name: 3-CHLORO-D-ALANINE METHYL ESTER,HYDROCHLORIDE
• Synonyms: 3-CHLORO-D-ALANINE METHYL ESTER,HYDROCHLORIDE;(R)-methyl 2-amino-3-chloropropanoate;(S)-Methyl 2-aMino-3-chloropropanoate hydrochloride;3-CHLORO-D-ALANINE METHYL ESTER;(S)-Methyl 2-amino-3-chloropropionate hydrochloride;3-Chloro-D-Ala-OMe hydrochloride;β-Chloro-D-alanine methyl ester hydrochloride;Cycloserine Impurity 3 (3-chloro-D-alanine methyl ester hydrochloride)
• CAS NO: 112346-82-4
• Molecular Formula: C₄H₈ClNO₂*ClH
• Molecular Weight: 174.03
• Mol File: 112346-82-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 149-152℃
• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sonicated), Methanol (Slightly)
• CAS DataBase Reference: 3-CHLORO-D-ALANINE METHYL ESTER,HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-D-ALANINE METHYL ESTER,HYDROCHLORIDE(112346-82-4)
• EPA Substance Registry System: 3-CHLORO-D-ALANINE METHYL ESTER,HYDROCHLORIDE(112346-82-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 112346-82-4(Hazardous Substances Data)

Usage

Description

3-Chloro-D-alanine Methyl Ester, Hydrochloride is a chemical compound that serves as an intermediate in the synthesis of antibiotic D-Cycloserine. 3-CHLORO-D-ALANINE METHYL ESTER,HYDROCHLORIDE plays a crucial role in the development of D-Cycloserine, which is known for its ability to inhibit cell wall biosynthesis in bacteria, thereby exerting antibacterial effects.

Uses

Used in Pharmaceutical Industry:
3-Chloro-D-alanine Methyl Ester, Hydrochloride is used as a key intermediate in the synthesis of D-Cycloserine, an antibiotic agent. It contributes to the production of D-Cycloserine, which is effective in inhibiting cell wall biosynthesis in bacteria, thus playing a significant role in combating bacterial infections.

Synthetic route

methanol (67-56-1) + D-serine-N-carboxyanhydride → (S)-methyl 2-amino-3-chloropropanoate hydrochloride (112346-82-4)

Conditions	Yield
With thionyl chloride at 25℃; for 2h; Temperature; Green chemistry;	94.72%

(S)-2-(2,6-dioxo-3-(3,4,5-trimethoxybenzamido)piperidin-1-yl)acetic acid (942123-68-4) + (S)-methyl 2-amino-3-chloropropanoate hydrochloride (112346-82-4) → (S)-methyl 3-chloro-2-(2-((S)-2,6-dioxo-3-(3,4,5-trimethoxybenzamido)piperidin-1-yl)acetamido)propanoate (942591-67-5)

Conditions	Yield
Stage #1: (S)-2-(2,6-dioxo-3-(3,4,5-trimethoxybenzamido)piperidin-1-yl)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; dimethyl sulfoxide at 0℃; Stage #2: D-β-Chloroalanine methyl ester hydrochloride With triethylamine In dichloromethane; dimethyl sulfoxide at 0 - 30℃;	68%

(S)-methyl 2-amino-3-chloropropanoate hydrochloride (112346-82-4) → (2S)-2-aziridinecarboxylic acid (1758-77-6)

Conditions	Yield
With sodium hydroxide In water at 90℃; for 0.166667h;	38%

Upstream product

• 67-56-1 methanol 

Downstream Products

• 1758-77-6 (2S)-2-aziridinecarboxylic acid 
• 942591-67-5 (S)-methyl 3-chloro-2-(2-((S)-2,6-dioxo-3-(3,4,5-trimethoxybenzamido)piperidin-1-yl)acetamido)propanoate 

Relevant articles and documents

Synthesis method of R-3-methyl closerine hydrochloride

The invention belongs to the field of drug synthesis, and discloses a synthesis method of R-3-methyl closerine hydrochloride. The synthesis method comprises the following steps: adding D-serine into paraformaldehyde, reacting at room temperature till small volume crystallization to obtain D-erine NCA; adding thionyl chloride into the D-erine NCA in methanol, and after reaction at room temperature,adding petroleum ether to obtain the R-3-methyl closerine hydrochloride. The method is simple in process operation, environmentally-friendly and mild in reaction conditions; the purity of the final product is up to 99 percent, and the yield is up to 94.72 percent, so that industrial production is facilitated.