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Chiral 3-substituted 3-vinyl-2-amino propionate and preparation method thereof

An aminopropionate and vinyl technology, which is applied in the field of 3-substituted 3-vinyl-2-aminopropionate and its preparation, and achieves the effects of mild reaction conditions, simple operation and strong substrate applicability

Inactive Publication Date: 2019-03-08
SHANGHAI UNIV OF MEDICINE & HEALTH SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, developing a strategy that provides a unified and predictable route for the stereoreactive construction of α-substituted α-AAs with vicinal stereocenters, selectively accessing all stereoisomers from the same starting material, remains an unmet challenge and has not been reported

Method used

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  • Chiral 3-substituted 3-vinyl-2-amino propionate and preparation method thereof
  • Chiral 3-substituted 3-vinyl-2-amino propionate and preparation method thereof
  • Chiral 3-substituted 3-vinyl-2-amino propionate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 5.4 mg (R, R, R)-L1 ligand and 3.36 mg (1,5-cyclooctadiene) iridium chloride dimer to a 5 ml reaction bottle, and add 0.5 ml Tetrahydrofuran and 0.5ml of n-propylamine were stirred at 50°C for 30 minutes, and the solvent was concentrated and spin-dried to obtain an iridium catalyst.

[0034] Add 4.5mg copper trifluoromethanesulfonate, 6.2mg (S, S p )-L2 ligand, under the condition of nitrogen protection, 1ml of tetrahydrofuran was added thereto, and stirred at 25°C for 30 minutes to obtain a copper catalyst.

[0035] Under nitrogen protection conditions, 48.0mg cinnamyl methyl carbonate, 65.7mg tert-butyl benzylidene aminoacetate, copper catalyst, iridium catalyst and 2ml tetrahydrofuran were added to a 10ml reaction flask, stirred at 30°C for 12 hours. Concentrate the reaction solution to dry the solvent, pass through a silica gel column to obtain the purified product (2S,3R)-2-amino-3-phenyl-4-pentenoic acid tert-butyl ester, the structural formula is as follows,...

Embodiment 2

[0039] Add 5.4 mg (R, R, R)-L1 ligand and 3.36 mg (1,5-cyclooctadiene) iridium chloride dimer to a 5 ml reaction bottle, and add 0.5 ml Tetrahydrofuran and 0.5ml of n-propylamine were stirred at 50°C for 30 minutes, and the solvent was concentrated and spin-dried to obtain an iridium catalyst.

[0040] Add 4.5mg copper trifluoromethanesulfonate, 6.2mg (S, S p )-L2 ligand, under the condition of nitrogen protection, 1ml of tetrahydrofuran was added thereto, and stirred at 25°C for 30 minutes to obtain a copper catalyst.

[0041] Under nitrogen protection, 58.5mg cinnamyl tert-butyl carbonate, 88.6mg dibenzylidene glycinate tert-butyl ester, copper catalyst, iridium catalyst and 2ml tetrahydrofuran were added to a 10ml reaction flask, and stirred at 30°C for 12 hours. Concentrate the reaction solution to dry the solvent, pass through a silica gel column to obtain the purified product (2S,3R)-2-amino-3-phenyl-4-pentenoic acid tert-butyl ester, the structural formula is as follow...

Embodiment 3

[0044] Add 5.4 mg (R, R, R)-L1 ligand and 3.36 mg (1,5-cyclooctadiene) iridium chloride dimer to a 5 ml reaction bottle, and add 0.5 ml Tetrahydrofuran and 0.5ml of n-propylamine were stirred at 50°C for 30 minutes, and the solvent was concentrated and spin-dried to obtain an iridium catalyst.

[0045] Add 4.5mg copper trifluoromethanesulfonate, 6.2mg (S, S p )-L2 ligand, under the condition of nitrogen protection, 1ml of tetrahydrofuran was added thereto, and stirred at 25°C for 30 minutes to obtain a copper catalyst.

[0046] Under nitrogen protection conditions, 48.0mg cinnamyl methyl carbonate, 88.6mg dibenzylidene glycinate tert-butyl ester, copper catalyst, iridium catalyst and 2ml tetrahydrofuran were added into a 10ml reaction flask, and stirred at 30°C for 12 hours. Concentrate the reaction solution to dry the solvent, pass through a silica gel column to obtain the purified product (2S,3R)-2-amino-3-phenyl-4-pentenoic acid tert-butyl ester, the structural formula is ...

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Abstract

The invention provides chiral 3-substituted 3-vinyl-2-amino propionate. The structural formula of the chiral 3-substituted 3-vinyl-2-amino propionate is as shown in specification. The invention further provides a method for synthesizing the 3-substituted 3-vinyl-2-amino propionate, and a reaction route of the method is as shown in specification. The chiral 3-substituted 3-vinyl-2-amino propionatehas the advantages of high substrate applicability, mild reaction conditions, simple operation, low synthesis cost and the like, and stereoscopic divergent synthesis of the 3-substituted 3-vinyl-2-amino propionate with continuous chiral centers can be implemented by only one-step reaction. The product can be directly applied to selective synthesis of an important chiral amino acid fragment of a marine natural product Hal ipeptin A with high anti-inflammatory activity, and thus, the original process is greatly shortened.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a novel compound, specifically a chiral 3-substituted 3-vinyl-2-aminopropionate and a preparation method thereof. Background technique [0002] α-substituted α-amino acids (α-AAs) are not only a class of important compounds that widely exist in organisms, but also participate in almost all life activities. In addition, α-AAs is also widely used as a basic structure in biochemical and pharmaceutical research. Due to the importance of α-AAs, it has attracted more and more attention from chemists, and also promoted the development of its asymmetric synthesis method. Indeed, many efficient methods have been reported for the synthesis of different types of enantiomerically enriched α-substituted α-AAs, and α-AAs can be obtained by simply choosing between a pair of enantiomeric catalysts. of the two enantiomers. However, the construction of α-AAs with vicinal stereocenters under full c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/36C07C227/06C07D307/54C07B43/04
CPCC07B43/04C07B2200/07C07C227/06C07D307/54C07C229/36
Inventor 孙振亮张万斌霍小红张嘉诚邢欣
Owner SHANGHAI UNIV OF MEDICINE & HEALTH SCI
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