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Method for preparing high-purity acetyl homotaurine

A technology of homotaurine and acetyl group is applied in the preparation field of synthesizing acetyl homotaurine, can solve the problems of difficult storage, harsh operation requirements, difficult quantification and the like, and achieves the effects of high yield and high product purity

Inactive Publication Date: 2015-04-01
北京华禧联合科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The invention provides a method for obtaining acetyl homotaurine by acetylation reaction. In the crystallization process of preparing acetyl homotaurine, it is necessary to provide acidic conditions for crystallization. In this invention, the acid chloride method is used to prepare Crystallization in the solution of hydrochloric acid solves the problems of difficult quantification, harsh operation requirements and difficult storage in the production process. It is suitable for production scale-up, with high yield and high product purity.

Method used

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  • Method for preparing high-purity acetyl homotaurine
  • Method for preparing high-purity acetyl homotaurine
  • Method for preparing high-purity acetyl homotaurine

Examples

Experimental program
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Embodiment 1

[0023] Example 1: Add 35 grams (252 mmol) of homotaurine into a 500 ml there-necked flask, add 300 ml of absolute ethanol, 58.50 grams of triethylamine (580 mmol) under stirring conditions, add 32.10 grams of acetic anhydride dropwise at room temperature, drop the mixture, and heat up Reflux reaction for 20-24 hours, add ice-water bath to cool down, dropwise add 45.74 g of acetyl chloride, dropwise at 20°C under temperature control, crystallize for 2 hours, filter, wash with 30ml of absolute ethanol, and dry under reduced pressure at 40°C to obtain 40.02 g of acetyl chloride For homotaurine, add 220ml of dichloromethane to reflux for 2 hours, filter, wash with 50ml of dichloromethane, and dry under reduced pressure at 40°C to obtain 22.5 g of acetyl homotaurine, HPLC: 99.35%, and homotaurine is less than 0.7%.

Embodiment 2

[0024] Example 2: Add 35 grams (252 mmol) of homotaurine into a 500 ml three-necked flask, add 300 ml of methylene chloride and 58.50 grams of triethylamine (580 mmol) under stirring, add 32.10 grams of acetic anhydride dropwise at room temperature, drop the mixture, and heat up Reflux reaction for 20-24 hours, add ice-water bath to cool down, add 55.34 g of acetyl chloride dropwise, add dropwise at 20°C under temperature control, crystallize for 2 hours, filter, wash with 30ml of absolute ethanol, and dry under reduced pressure at 40°C to obtain 45.02 g of acetyl chloride For homotaurine, add 220ml of dichloromethane to reflux for 2 hours, filter, wash with 50ml of dichloromethane, and dry under reduced pressure at 40°C to obtain 20.5 g of acetyl homotaurine, HPLC: 99.75%, and homotaurine is less than 0.7%.

Embodiment 3

[0025] Example 3: Add 35 grams (252 mmol) of homotaurine to a 500 ml three-necked flask, add 300 ml of absolute ethanol and 58.50 grams of triethylamine (580 mmol) under stirring, add 32.10 grams of acetic anhydride dropwise at room temperature, drop the mixture, and heat up Reflux reaction for 20-24 hours, add ice-water bath to cool down, add 67.72 grams of concentrated hydrochloric acid dropwise, add dropwise under temperature control at 20°C, crystallize for 2 hours, filter, wash with 30ml of absolute ethanol, and dry under reduced pressure at 40°C to obtain 44.02 grams of acetyl For homotaurine, add 220ml of anhydrous room temperature beating for 2 hours, filter, wash with 50ml of dichloromethane, and dry under reduced pressure at 40°C to obtain 18.5 g of acetyl homotaurine, HPLC: 99.05%, and homotaurine is less than 0.7%.

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Abstract

The invention belongs to the technical field of pharmaceutical chemistry and particularly relates to a preparation method for synthesizing acetyl homotaurine (an intermediate of acamprosate calcium).The method comprises the steps of allowing acetic anhydride to react with homotaurine to prepare acetyl homotaurine, and crystallizing acetyl homotaurine by a method of substituting a hydrochloric acid alcohol solution in a post-treatment process. The synthesis method is strong in controllability, simple and convenient in technology and high in yield, avoids the disadvantage that hydrochloric acid alcohol is difficult to store, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a preparation method for synthesizing acetyl homotaurine (intermediate of calcium acamprosate). The commonly used starting material is homotaurine, and acetylated homotaurine is prepared through acetylation, and the commonly used acetylation reagents are acetyl chloride, acetic acid, acetic anhydride, etc. Background technique [0002] Acetyl homotaurine is an intermediate in the synthesis of calcium acamprosate. The structure of calcium acamprosate is similar to the human endogenous neurotransmitter γ-aminobutyric acid (GABA). Its main pharmacological effect is to quit alcohol dependence. Calcium acamprosate is recorded in European Pharmacopoeia 6.0, but the inspection of related substances has not been reported. Wuhan Wuyao Pharmaceutical Group developed and synthesized the raw material. In this paper, a more detailed quality study was carried out on a...

Claims

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Application Information

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IPC IPC(8): C07C309/15C07C303/22C07C303/44
Inventor 李加贺庄伟平毕华
Owner 北京华禧联合科技发展有限公司
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