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The preparation method of n-substituted phenylglycine

A technology of phenylglycine and aniline, which is applied in the field of preparation of N-substituted phenylglycine (dabigatran etexilate intermediate), can solve the problems of poor purity, low yield and high cost, and achieve low raw material prices and high product quality. The effect of high purity and yield and low equipment requirements

Active Publication Date: 2016-08-24
ABA CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In this type of method, taking chloroacetic acid as the raw material product has poor purity and low yield
With bromoacetic acid as raw material, the cost is higher

Method used

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  • The preparation method of n-substituted phenylglycine
  • The preparation method of n-substituted phenylglycine
  • The preparation method of n-substituted phenylglycine

Examples

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Embodiment Construction

[0022] The following are specific embodiments of the present invention, further describing the technical solution of the present invention, but the present invention is not limited to this embodiment.

[0023] (1) Synthesis of N-p-cyanophenylglycine (1)

[0024] In a 1000 mL hydrogenation reactor, add 45.9 g of 50% (w / w) glyoxylic acid aqueous solution, 500 ml of methanol, 0.5 g of palladium-carbon with 5% (w / w) palladium loading, and 35.4 g of 4-aminobenzonitrile, at room temperature (18~25°C) After stirring for 30 minutes, replace the system with hydrogen (referring to the gas in the reactor when feeding is air, at this time it is replaced with hydrogen, and the pressure is maintained at 10atm; this is a professional control process for production, and it cannot be added to 10atm at the beginning. , when the temperature rises, the pressure will rise, and the reaction will release heat at the same time, and the temperature will rise further. Generally, 2 to 3 atm hydrogen wil...

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Abstract

The invention discloses a preparation method of N-substituted phenylglycine (dabigatran etexilate intermediate) which has not been reported in literature. The process of the method is as follows: using inexpensive and easily available substituted aniline (1) as a starting material, condensing with glyoxylic acid to form an imine, and simultaneously hydrogenating and reducing to obtain N-(substituted phenyl)glycine. The synthetic route has not been reported in the literature, and the raw materials are cheap and easy to obtain; the unit operation is simple, the equipment requirements are low, and it is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of N-substituted phenylglycine (dabigatran etexilate intermediate). Background technique [0002] N-substituted phenylglycine is an important intermediate of the new anticoagulant drug Dabigatran Etexilate developed and marketed by Boehringer Ingelheim, Germany. The synthesis method of its literature reports (WO2012009678, WO2009111997, CN1861596, US20050107355, etc.) is as follows : [0003] [0004] In this type of method, taking chloroacetic acid as the raw material product has poor purity and low yield. With bromoacetic acid as raw material, the cost is higher. Contents of the invention [0005] The technical problem to be solved by the present invention is to provide a new preparation method of N-substituted phenylglycine (dabigatran etexilate intermediate). [0006] The technical scheme that the present invention solves its technical problem to take is: [0007] A preparation method of N-subs...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/58C07C253/30C07D271/07
CPCC07D271/07C07C253/30C07C255/58
Inventor 林志刚刘艳琴徐军江岳恒蔡彤
Owner ABA CHEM CORP
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