Alpha,beta-diamino acid derivative, synthetic method thereof and application thereof

A technology of two amino acids and synthetic methods, applied in the α field, can solve the problems of difficult large-scale industrial application, cumbersome operation and post-processing, and limited economic value, and achieve wide substrate applicability, high atom economy, and low cost Effect

Inactive Publication Date: 2011-08-17
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, although a series of different routes and synthetic methods have been developed (Org.Prep.Proc.Int.1996,28,333; Tetrahedron Lett.2003,44,4865; Tetrahedron Lett.1996,37,2261; Org.Lett .2004,6,213.), but many of these routes and synthetic methods (Chem.Rev.2005,105,3167-3196) have shortcomings such as long steps, high

Method used

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  • Alpha,beta-diamino acid derivative, synthetic method thereof and application thereof
  • Alpha,beta-diamino acid derivative, synthetic method thereof and application thereof
  • Alpha,beta-diamino acid derivative, synthetic method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] N-(4-bromobenzylidene)-4-chloroaniline (0.7mmol, 1.0eq), CbzNH 2 (1.4mmol, 2.0eq), rhodium acetate (0.007mmol) and Molecular sieves (0.2g) were dissolved in 1,2-dichloroethane (5.0ml) at room temperature, and then, dissolved in 1,2-dichloroethane (2.0ml) The ester (1.4mmol, 2.0eq) was added dropwise to the reaction system within 1 hour. After the dropwise addition was completed, it was stirred for 0.5 hour, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:50~1:20) to obtain the product (2S*, 3R*)-2-(benzyloxycarbonylamino)-3-(4-bromophenyl )-3-(4-Chloroanilino)-2-phenylpropanoic acid methyl ester, the yield is 72%, and the dr value is greater than 20:1. The structural formula of the product is shown in the following formula, and its NMR 1 H NMR, 13 C NMR spectrum see figure 1 .

[0065]

Embodiment 2

[0067] N-(4-bromobenzylidene)-4-chloroaniline (0.7mmol, 1.0eq), CbzNH 2 (1.4mmol, 2.0eq), rhodium propionate (0.007mmol) and Molecular sieves (0.2g) were dissolved in toluene (5.0ml) at room temperature, and then ethyl benzyldiazoacetate (1.4mmol, 2.0eq) dissolved in toluene (2.0ml) was added dropwise to In the reaction system, after the dropwise addition was completed, the mixture was stirred for 0.5 hour, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:50~1:20) to obtain the product (2S*, 3R*)-2-benzyl-2-(benzyloxycarbonylamino)-3-( 4-bromophenyl)-3-(4-chloroanilino)propionic acid methyl ester, the yield is 68%, and the dr value is greater than 20:1. The structural formula of the product is shown in the following formula, and its NMR 1 H NMR, 13 C NMR spectrum see figure 2 .

[0068]

Embodiment 3

[0070] N-benzylidene aniline (0.7mmol, 1.0eq), CbzNH 2 (1.4mmol, 2.0eq), rhodium butyrate (0.007mmol) and Molecular sieves (0.2g) were dissolved in dichloromethane (5.0ml) at room temperature, then methyl phenyldiazoacetate (1.4mmol, 2.0eq) dissolved in dichloromethane (2.0ml) was dissolved in 1 hour It was added dropwise to the reaction system, and after the dropwise addition was completed, it was stirred for 0.5 hours, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:50~1:20) to obtain the product (2S*,3R*)-2-(benzyloxycarbonylamino)-2,3-diphenyl- Methyl 3-(anilino)propionate with a yield of 50% and a dr value greater than 20:1. The structural formula of the product is shown in the following formula, and its NMR 1 H NMR, 13 C NMR spectrum see image 3 .

[0071]

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Abstract

The invention relates to an alpha,beta-diamino acid derivative, and a synthetic method and application thereof. The alpha,beta-diamino acid derivative is shown as a structural formula (A). The synthetic method comprises the following steps of: dissolving imide, amide, a catalyst and a molecular sieve in solvent, dripping a diazo compound into the mixture, and after reacting with stirring, and removing the solvent by reduced pressure distillation to obtain a coarse product; and purifying by column chromatography to obtain the alpha,beta-diamino acid derivative. The synthetic method has the advantages of high atom economy, selectivity and yield, mild reaction conditions and simplicity and safety of operation. The alpha,beta-diamino acid derivative is an important intermediate of chemical engineering and medicines, is widely applied to the field of pharmaceutical chemical engineering; and due to a certain of anticancer activity, the alpha,beta-diamino acid derivative has the wide application prospect in the field of the pharmaceutical chemical engineering.

Description

technical field [0001] This patent relates to the field of synthetic medicine and chemical industry, mainly an α, β-diamino acid derivative and its synthesis method and application. Background technique [0002] α, β-Diamino acid derivatives are a kind of important skeleton structures for building natural products and synthetic drugs, and many marine organisms and natural antibiotics contain such skeleton structures. For example, there are such skeleton structures in many drug structures such as antineoplastic drugs bleomycin and peplomycin, and tuberculosis drug viomycin. α,β-Diamino acid derivatives can also be used in the synthesis of numerous other antineoplastic drugs, antibiotics, antifungal drugs. In addition, α,β-diamino acid derivatives can be used as ligands (Inorg. Biochem. 1995, 57, 279.) and synthetic building blocks to synthesize a series of biologically active compounds. In addition, it has a strong chelating effect with metals, and this property provides br...

Claims

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Application Information

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IPC IPC(8): C07C271/22C07C269/06A61K31/27A61P35/00
Inventor 胡文浩席建备张霞江俊赵政张莉
Owner EAST CHINA NORMAL UNIVERSITY
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