A synthetic method of (R)-methyl 2-amino-3-chloropropanoate hydrochloride

Abstract

A synthetic method of (R)-methyl 2-amino-3-chloropropanoate hydrochloride is disclosed. The method includes steps of 1) dissolving D-serine into methanol, adding thionyl chloride dropwise into the methanol, performing a refluxing reaction to achieve methyl esterification, concentrating methanol until a product is dry, adding ethyl acetate, pulping at room temperature, and performing filtration, rinsing and drying to obtain D-serine methyl ester hydrochloride, and 2) adding the D-serine methyl ester hydrochloride and thionyl chloride into dichloroethane, performing chlorination for 24 h, performing filtration to obtain a crude (R)-methyl 2-amino-3-chloropropanoate hydrochloride product, decoloring the crude product in methanol, cooling, crystallizing and then performing filtration and drying. The method is high in yield, side products are less, a mother liquor after the reaction can be recycled after treatment, and the production cost is reduced. Tail gas generated by the method can be absorbed by a strong alkaline solution to form a salt, and the generated salt is then separated and reutilized, thus achieving environment friendly requirements.

Description

technical field [0001] The invention relates to the field of medicament synthesis, in particular to a method for synthesizing R-chlorserine methyl ester hydrochloride. Background technique [0002] Antibiotics are a class of secondary metabolites produced by microorganisms (including bacteria, fungi, actinomycetes) or higher animals and plants in the course of life, which have anti-pathogen or other activities, and can interfere with the development of other living cells. Chemical substances . Antibiotics commonly used in clinical practice include genetically modified engineering bacteria, extracts from culture fluid, and chemically synthesized or semi-synthesized compounds. Cycloserine, also known as D-4-amino-3-isoxazolidinone, is an antibiotic drug that has a good inhibitory effect on Mycobacterium tuberculosis. Because bacteria are not easy to develop drug resistance to it, it is mainly used clinically to treat the infection of drug-resistant Mycobacterium tuberculosis...

AI Technical Summary

Problems solved by technology

R-Chloroserine methyl ester hydrochloride is an important intermediate of cycloserine, and there is no report on the synthesis of R-Chloroserine methyl ester hydrochloride at home and abroad