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

A technology of chlorserine methyl ester and serine methyl ester, which is applied in the field of synthesis of R-chlorserine methyl ester hydrochloride to achieve the effects of less by-products, high yield and reduced production cost

Inactive Publication Date: 2017-03-22
安徽省诚联医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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

Method used

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Examples

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Embodiment 1

[0013] A kind of synthetic method of R-chloroserine methyl ester hydrochloride, concrete steps are as follows:

[0014] Step 1, preparation of D-serine methyl ester hydrochloride: Add 1200ml methanol and 250g D-serine into a 2000ml three-necked flask, cool down to below 25°C, add 450g of thionyl chloride dropwise, and control the dropping time within 2 hours After the dropwise addition, the temperature was raised to reflux and the reaction was continued for 6 hours. After the reflux reaction was completed, methanol was concentrated to dryness, 1000ml ethyl acetate was added to make a slurry, and then filtered and dried to obtain D-serine methyl ester hydrochloride. The concentrated methanol can be applied to the reaction step, and the ethyl acetate mother liquor can be applied to the beating step after distillation;

[0015] Step 2: Add 150g of the first step intermediate and 150g of thionyl chloride into 1500ml of dichloroethane, and carry out chlorination reaction at 45°C fo...

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PUM

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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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/16C07C229/22
CPCC07C227/16C07C227/18
Inventor 刘辉
Owner 安徽省诚联医药科技有限公司
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