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

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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 est

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 invention relates to a preparation method of glutamic acid, in particular to a preparation method of glutamic acid-5-benzyl-1-tert-butyl hydrochloride. Background technique [0002] Glutamate-5-benzyl-1-tert-butyl ester hydrochloride is a commonly used amino acid protective agent, which is often used in the field of peptide synthesis. The previous synthetic route was to esterify glutamic acid with benzyl alcohol to obtain gluten. 5-benzyl glutamate, dichloromethane as solvent, p-toluenesulfonic acid as catalyst, 5-benzyl glutamate reacts with isobutylene to obtain 5-benzyl glutamate-1-tert-butyl ester, and finally Glutamate-5-benzyl-1-tert-butyl ester is dissolved in ether, and hydrochloric acid gas is passed through to prepare glutamate-5-benzyl-1-tert-butyl hydrochloride. In fact, this route is difficult to produce. First, the solubility of 5-benzyl glutamate in dichloromethane is small, and the yield of the incomplete reaction is low; second, the in...

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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