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Method for synthesizing substituted amino carboxylic acid by ugi reaction

A technology of aminocarboxylic acid and Uji reaction, which is applied in the field of synthesizing substituted aminocarboxylic acids by Uji reaction, which can solve the problems of harsh reaction conditions and low industrialization level, and achieve the effect of reasonable selection of reaction process and avoiding low yield

Active Publication Date: 2012-12-12
上海药明康德新药开发有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a simple synthetic method for substituted aminocarboxylic acids, which mainly solves the technical problems of harsh reaction conditions and low degree of industrialization in existing synthetic methods

Method used

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  • Method for synthesizing substituted amino carboxylic acid by ugi reaction
  • Method for synthesizing substituted amino carboxylic acid by ugi reaction
  • Method for synthesizing substituted amino carboxylic acid by ugi reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0011] 1 Preparation of dipeptide protected by tert-butyl group:

[0012] Add anhydrous methanol (100ml) to a dry 100ml round-bottomed flask, then add 4-cyanobenzaldehyde (1g, 7.63mmol), replace nitrogen in the reaction flask three times, and slowly add 3-Methylbenzylamine (0.925 g, 7.63 mmol) kept the reaction temperature not higher than 10 °C. After the feeding is completed, the solution turns yellow. After stirring and reacting for 1 hour at 10°C, 2-fluoro-5-methylbenzoic acid (1.18g, 7.63mmol) and tert-butylisocyanate (0.641g, 7.63mmol) are sequentially added under nitrogen protection. ), keep the reaction temperature not higher than 10°C, after feeding is completed, the reaction solution is raised to room temperature and stirred for 24 hours. Until TLC (petroleum ether / ethyl acetate=5:1) detected that the starting material disappeared, the reaction was complete. The reaction solution was spin-dried under reduced pressure. The product 1 (3.32 g, 7.04 mmol) was obtained ...

Embodiment 2

[0019] 1 Preparation of dipeptide protected by tert-butyl group:

[0020] Add anhydrous methanol (100ml) to a dry 100ml round-bottomed flask, then add 4-cyanobenzaldehyde (1g, 7.63mmol), replace nitrogen in the reaction flask three times, and slowly add 3-Methylbenzylamine (0.925 g, 7.63 mmol) kept the reaction temperature not higher than 10 °C. After the feeding is completed, the solution turns yellow. After stirring and reacting for 1 hour at 10°C, 2-fluoro-5-methylbenzoic acid (1.18g, 7.63mmol) and tert-butylisocyanate (0.641g, 7.63mmol) are sequentially added under nitrogen protection. ), keep the reaction temperature not higher than 10°C, after feeding is completed, the reaction solution is raised to room temperature and stirred for 24 hours. Until TLC (petroleum ether / ethyl acetate=5:1) detected that the starting material disappeared, the reaction was complete. The reaction solution was spin-dried under reduced pressure. The product 1 (3.32 g, 7.04 mmol) was obtained ...

Embodiment 3

[0027] 1 Preparation of dipeptide protected by tert-butyl group:

[0028] Add anhydrous methanol (100ml) to a dry 100ml round-bottomed flask, then add 4-cyanobenzaldehyde (1g, 7.63mmol), replace nitrogen in the reaction flask three times, and slowly add 3-Methylbenzylamine (0.925 g, 7.63 mmol) kept the reaction temperature not higher than 10 °C. After the feeding is completed, the solution turns yellow. After stirring and reacting for 1 hour at 10°C, 2-fluoro-5-methylbenzoic acid (1.18g, 7.63mmol) and tert-butylisocyanate (0.641g, 7.63mmol) are sequentially added under nitrogen protection. ), keep the reaction temperature not higher than 10°C, after feeding is completed, the reaction solution is raised to room temperature and stirred for 24 hours. Until TLC (petroleum ether / ethyl acetate=5:1) detected that the starting material disappeared, the reaction was complete. The reaction solution was spin-dried under reduced pressure. The product 1 (3.32 g, 7.04 mmol) was obtained ...

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Abstract

The invention relates to a method for synthesizing substituted amino carboxylic acid, in particular to a method for synthesizing the substituted amino carboxylic acid by utilization of Ugi reaction. The method mainly solves the technical problems of rigorous reaction conditions and low industrialization degree in the prior synthesis method. The method adopts the technical proposal that the method adopts tert-butyl isonitrile which can be obtained by commercialization as a raw material, obtains corresponding t-butyl carboxamide through the Ugi reaction, and obtains the substituted amino carboxylic acid by mildly hydrolyzing the t-butyl carboxamide under the action of trifluoroacetic acid and water. The synthesis technology is as shown in the formula. In the technology, R, R1 and R2 refer to alkyl groups or aryl groups between C1 and C20; the volume ratio of the trifluoroacetic acid to the water in the second step, namely TFA:H2O, is between 1:5 and 100:0; and the reaction temperature is between the room temperature and the solvent reflux temperature.

Description

Technical field: [0001] The invention relates to a method for synthesizing substituted aminocarboxylic acids, in particular to a method for synthesizing substituted aminocarboxylic acids by Ugi reaction. Background technique: [0002] Ugi reaction is a relatively useful method for the synthesis of amino acids and peptide compounds. When using Ugi reaction to synthesize substituted aminocarboxylic acids, it is necessary to hydrolyze the terminal amide into carboxylic acid. Due to the existence of multiple amide groups, many known hydrolysis The conditions are relatively harsh, and sometimes it is difficult to selectively obtain the corresponding carboxylic acid. In addition, many isonitriles are not commercially available starting materials. Therefore, it is necessary to develop a method for synthesizing the corresponding amide 1 using commercially available isonitriles, which is then easily hydrolyzed. [0003] Invention content: [0004] The purpose of the present in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/10C07C233/87
Inventor 张科许金峰高兴柱彭宪施一峰马汝建陈曙辉李革
Owner 上海药明康德新药开发有限公司
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