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Preparation method of glutamic acid-5-benzyl ester-1-tert-butyl ester hydrochloride

A technology of tert-butyl acetate and glutamic acid, which is applied in the field of preparation of glutamic acid-5-benzyl ester-1-tert-butyl ester hydrochloride, can solve problems such as difficulty in production and operation, achieve higher yield, Avoid overly acidic, high-safety effects

Inactive Publication Date: 2016-05-04
GL BIOCHEM SHANGHAI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a preparation method of glutamic acid-5-benzyl ester-1-tert-butyl ester hydrochloride, which mainly solves the technical problem that existing synthetic methods are difficult to produce and operate

Method used

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  • Preparation method of glutamic acid-5-benzyl ester-1-tert-butyl ester hydrochloride
  • Preparation method of glutamic acid-5-benzyl ester-1-tert-butyl ester hydrochloride

Examples

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Embodiment 1

[0017] Example 1: Add 34ml of concentrated sulfuric acid dropwise to 340ml of ether, keep below 10°C, add 340ml of benzyl alcohol, stir for 15 minutes, evaporate the ether under reduced pressure at room temperature, add 50g of L-glutamic acid and stir for 20 hours. Adjust pH to 7-8 with ethylamine, filter and dry to obtain 75g of L-glutamate-5-benzyl ester; add 75g of L-glutamate-5-benzyl ester to 750ml of tert-butyl acetate, cool with ice water for external use, T figure 1 , 2 .

Embodiment 2

[0018] Example 2: Add 34ml of concentrated sulfuric acid dropwise to 340ml of ether, keep below 10°C, add 340ml of benzyl alcohol, stir for 15 minutes, evaporate the ether under reduced pressure at room temperature, add 50g of L-glutamic acid and stir for 20 hours. Adjust pH to 7-8 with ethylamine, filter and dry to obtain 75g of L-glutamate-5-benzyl ester; add 75g of L-glutamate-5-benzyl ester to 750ml of tert-butyl acetate, cool with ice water for external use, T figure 1 , 2 .

Embodiment 3

[0019] Example 3: Add 34ml of concentrated sulfuric acid dropwise to 340ml of ether, keep below 10°C, add 340ml of benzyl alcohol, stir for 15 minutes, evaporate the ether under reduced pressure at room temperature, add 50g of L-glutamic acid and stir for 20 hours. Adjust pH to 7-8 with ethylamine, filter and dry to obtain 75g of L-glutamate-5-benzyl ester; add 75g of L-glutamate-5-benzyl ester to 750ml of tert-butyl acetate, cool with ice water for external use, T figure 1 , 2 .

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Abstract

A preparation method of glutamic acid-5-benzyl ester-1-tert-butyl ester hydrochloride mainly solves the problem of operation difficulty in the synthesis method of the prior arts. A technical scheme is as below: the preparation method of glutamic acid-5-benzyl ester-1-tert-butyl ester hydrochloride comprises the steps of: esterifying a starting material of glutamic acid with benzyl alcohol, and purifying to obtain glutamic acid 5-benzyl ester; conducting a transesterification reaction on glutamic acid 5-benzyl ester and tert-butyl acetate under catalysis to obtain glutamic acid-5-benzyl ester-1-tert-butyl ether; and finally controlling the atmosphere with ether hydrochloric acid to an acidic state to obtain the glutamate 5-benzyl-1-t-butyl ester hydrochloride. The product can be used for the field of peptide synthesis.

Description

Technical field [0001] The present invention relates to a method for preparing glutamic acid, in particular to a method for preparing glutamic acid-5-benzyl ester-1-tert-butyl ester hydrochloride. Background technique [0002] Glutamic acid-5-benzyl ester-1-tert-butyl ester hydrochloride is a commonly used amino acid protecting agent. It is often used in the field of polypeptide synthesis. The previous synthesis route was to esterify glutamic acid with benzyl alcohol to obtain glutamic acid. Glutamic acid-5-benzyl ester, then dichloromethane is used as the solvent, p-toluenesulfonic acid is used as the catalyst, glutamic acid-5-benzyl ester reacts with isobutylene to obtain glutamic acid-5-benzyl ester-1-tert-butyl ester, and finally Glutamic acid-5-benzyl ester-1-tert-butyl ester is dissolved with diethyl ether, and hydrochloric acid gas is introduced to prepare glutamic acid-5-benzyl ester-1-tert-butyl ester hydrochloride. In fact, this route is quite difficult to produce...

Claims

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Application Information

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IPC IPC(8): C07C229/24C07C227/18
CPCC07C227/18
Inventor 徐红岩窦肖俊
Owner GL BIOCHEM SHANGHAI
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