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Anti-racemization preparation method of D-(+)-alpha-(2-thienylethamino)-alpha-(2-chlorophenyl) acetate hydrochloride

A technology of thienylethylamine and o-chlorophenylglycine methyl ester, which is applied in the field of preparation of D--α--α-methyl acetate hydrochloride, to achieve the effect of reducing the degree of racemization

Inactive Publication Date: 2010-10-13
启东东岳药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no literature report on how to prevent racemization during the preparation of D-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)methyl acetate hydrochloride

Method used

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  • Anti-racemization preparation method of D-(+)-alpha-(2-thienylethamino)-alpha-(2-chlorophenyl) acetate hydrochloride
  • Anti-racemization preparation method of D-(+)-alpha-(2-thienylethamino)-alpha-(2-chlorophenyl) acetate hydrochloride

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Embodiment 1

[0014] 60 grams of refined dry product of S-o-chlorophenylglycine methyl ester-L-tartrate, 180 ml of chloroform, and 60 grams of water were put into a 500 ml reactor. Cool to below 10°C. Add ammonia water dropwise at 10°C to adjust the pH to 8-9, stir for 0.5 hours, let stand for 30 minutes, separate layers, extract the water layer with 50ml of chloroform, combine the chloroform layers, wash with 100ml of water, and drain the water layer. The chloroform layer was concentrated under reduced pressure to 55-60°C, and the vacuum degree was -0.095~-0.090Mpa to obtain about 34g of S-o-chlorophenylglycine methyl ester as a light yellow oily product, with a yield of 99%.

[0015] 180 grams of the above-mentioned S-o-chlorophenylglycine methyl ester, dehydrated and deacidified acetonitrile (acetic acid content less than 0.01%, moisture less than 0.05%), 60 grams of sulfonate, and 40 grams of dipotassium hydrogen phosphate were added in a 500ml reactor. After the addition is complete, ...

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Abstract

The invention discloses an anti-racemization preparation method of D-(+)-alpha-(2-thienylethamino)-alpha-(2-chlorophenyl) acetate hydrochloride. In the method, S-Chlorophenylglycine methyl ester reacts with sulphonate, acetonitrile is used as a solvent, and the content of acetic acid in the acetonitrile is less than 0.01 percent. The invention can effectively reduce the racemization degree through controlling the processing conditions of the moisture and the acidity of the solvent, the reaction temperature, the reaction time and the like.

Description

Technical field: [0001] The invention relates to a preparation method of D-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)methyl acetate hydrochloride. Background technique: [0002] D-(+)-α-(2-thiopheneethylamino)-α-(2-chlorophenyl)methyl acetate hydrochloride is a key intermediate of the anti-platelet aggregation drug Clopidogrel. The structure is as follows: [0003] [0004] The preparation method of D-(+)-α-(2-thiopheneethylamino)-α-(2-chlorophenyl)methyl acetate hydrochloride has been reported in literature and patents, and S-o-chlorophenylglycine is generally used Methyl ester-L-tartrate is free and prepared by substitution reaction with 2-thiophenethanol p-toluenesulfonate. The reaction principle is as follows: [0005] [0006] U.S. Patent No. 504469 reports that acetonitrile is used as a solvent, and dipotassium hydrogen phosphate is used as an acid-binding agent. React at 80°C for 40 hours to obtain a product with an optical rotation of 104° (c=1, methanol...

Claims

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Application Information

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IPC IPC(8): C07D333/20
Inventor 龙中柱李林旺吴福忠蔡水洪吴雄
Owner 启东东岳药业有限公司
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