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A kind of synthetic method of acrylic acid derivative

A synthesis method and a derivative technology, applied in the direction of organic chemistry, etc., can solve the problem of no literature report in the synthesis, and achieve the effect of simple reaction operation and high yield.

Active Publication Date: 2020-09-01
成都道合尔医药技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, there is no literature on the synthesis of (S)-2-(2-(tert-butoxycarbonylamino)-3-(1-trityl-1H-imidazole-4-yl) propionamide) acrylic acid to report

Method used

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  • A kind of synthetic method of acrylic acid derivative
  • A kind of synthetic method of acrylic acid derivative
  • A kind of synthetic method of acrylic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-(1-trityl-1H-imidazole-4-yl)propionamide)-3-hydroxypropionate preparation of

[0023]

[0024] Dissolve (S)-2-(tert-butoxycarbonylamino)-3-(1-trityl-1H-imidazole-4-yl)propionic acid 2200g (4.42mol, 1.0eq) in dimethylformamide In 15L, add pyridine 1042g (13.17mol, 3.0eq), add serine methyl ester hydrochloride 753g (4.84mol, 1.1eq); add EDCI 1011g (5.30mol, 1.2eq) in batches, control the internal temperature to less than 15°C, After addition, react at 20-30°C for 3h. The reaction solution was poured into 45 L of ice water, and a large amount of solids precipitated out. Filter, dissolve the filter cake with 15L of EA / THF=5 / 1, wash once with 5L of 1N HCl, wash once with 5L of saturated saline, and dry sodium sulfate. Filter, concentrate the organic phase under reduced pressure until a large amount of solids precipitate, add 5L of petroleum ether to make a slurry, filter, and dry to obtain 2-((S)-2-(tert-butoxycar...

Embodiment 2

[0025] Example 2: 2-((S)-2-(tert-butoxycarbonylamino)-3-(1-trityl-1H-imidazole-4-yl)propionamide)-3-methanesulfonyloxy Preparation of methyl propionate:

[0026]

Embodiment 3

[0028] Example 3: Preparation of (S)-2-(2-(tert-butoxycarbonylamino)-3-(1-trityl-1H-imidazole-4-yl)propionamide)methyl acrylate:

[0029]

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Abstract

The invention belongs to the technical field of organic synthesis and provides a synthetic method of an acrylic acid derivative. The synthetic method comprises the following steps of by taking (S)-2-(tert-butoxycarbonylaminoethyl)-3-(1-triphenylmethyl-1H-imidazole-4-yl)propanoic acid as a raw material, performing EDCI condensation on (S)-2-(tert-butoxycarbonylaminoethyl)-3-(1-triphenylmethyl-1H-imidazole-4-yl)propanoic acid and serine methyl ester hydrochloride EDCI, performing methylsulfonyl chloride acylation, eliminating organic alkali, hydrolyzing inorganic alkali to obtain (S)-2-(2-(tert-butoxycarbonylaminoethyl)-3-(1-triphenylmethyl-1H-imidazole-4-yl)propanamide) acrylic acid with four steps. The whole reaction is simple to operate and relatively high in yield and can be used for large-scale production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing acrylic acid derivatives. Background technique [0002] Histidine is one of the essential amino acids for humans. Its main function is to maintain the healthy development of various tissues in the body, especially the myelin sheath that wraps nerve cells, and ensures the transmission of information from the brain to various parts of the body. It has a certain effect on the treatment of mental illness, rheumatoid arthritis, deafness caused by nerve damage, nephrogenic anemia and uremia. In addition, polypeptides containing histidine structural units also have various biological activities. In 2000, Mao Yumin and others discovered that a polypeptide containing a histidine fragment had therapeutic effects on arrhythmia, bronchial asthma, acute pancreatitis, diabetes, and albinism (CN1342770A). In 2016, Wu Junchen and others from East China Uni...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/64
CPCC07D233/64
Inventor 宁兆伦雷东魏庚辉黄湘川
Owner 成都道合尔医药技术有限公司
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