Kinetic resolution method of chiral amine

A kinetic separation, chiral amine technology, applied in fermentation and other directions, can solve the problems of high environmental pollution, low optical purity of products, low separation yield, etc., and achieves improved performance, great application value, and mild reaction conditions. Effect

Inactive Publication Date: 2012-11-07
六安佳诺生化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has problems such as low resolution yield, low optical purity of the product, and large environmental pollution.

Method used

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  • Kinetic resolution method of chiral amine
  • Kinetic resolution method of chiral amine
  • Kinetic resolution method of chiral amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 1-(1-naphthyl)ethylamine and S-styroyl acetate in a molar ratio of 1:0.5 to a toluene solvent 10 times the volume of the chiral amine to form 1-(1-naphthyl)ethane Novozymes 435 was added at a mass fraction of 10% of the amine, and reacted for 48 hours at a reaction temperature of 30°C to obtain R-1-acetylnaphthylethylamine with a conversion rate of 50% and an e.e value >99%.

Embodiment 2

[0018] Add 1-(2-naphthyl)ethylamine and S-styroyl acetate in a molar ratio of 1:3 to a toluene solvent 10 times the volume of the chiral amine to form 1-(2-naphthyl)ethylamine Novozymes 435 was added at a mass fraction of 80% of the amine, and reacted for 12 hours at a reaction temperature of 70°C to obtain R-2-acetylnaphthylethylamine with a conversion rate of 50% and an e.e value >99%.

Embodiment 3

[0020] Add 1-(1-naphthyl)ethylamine and R-styroyl acetate in a molar ratio of 1:2 to a toluene solvent 10 times the volume of the chiral amine to form 1-(1-naphthyl)ethylamine Novozymes 435 was added at a mass fraction of 40% of the amine, and reacted for 24 hours at a reaction temperature of 70°C to obtain S-1-acetylnaphthylethylamine with a conversion rate of 50% and an e.e value >99%.

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Abstract

The invention discloses a kinetic resolution method of chiral amine, comprising the following steps of: adding chiral amine and acyl donor at the mol ratio of 1:0.5-3 into an organic solvent reaction system, adding lipase which accounts for 10-80 wt% of the weight of chiral amine, and reacting at the reaction temperature of 30-70 DEG C for 12-48 hours to obtain amide with the conversion rate of 50% and e.e value being greater than 99%. According to the invention, resolution of chiral amine can be mildly realized under the condition of enzyme catalysis; and simultaneously, the product has good optical purity, high yield and great application values.

Description

field of invention [0001] The invention relates to a kinetic resolution method, in particular to a dynamic resolution method for chiral amines. Background technique [0002] Chiral amines with a single configuration are commonly used intermediates in the synthesis of chiral drugs, and can also be used as chiral bases to resolve various chiral acids. In industry, when preparing these optically pure chiral amines, the resolution of racemates is still the most important and practical method because of its economy and feasibility. The most important resolution method for 1-(1-naphthyl)ethylamine and 1-(2-naphthyl)ethylamine is to use D-tartaric acid as the chiral resolution reagent for chemical resolution. This method has problems such as low resolution yield, low optical purity of the product, and large environmental pollution. [0003] How to achieve high-efficiency and green separation of chiral amines while ensuring high optical purity has become our goal. Invention cont...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P13/00
Inventor 王际宽
Owner 六安佳诺生化科技有限公司
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