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Kinetic resolution method of secondary alcohol

A technology of kinetic resolution and secondary alcohol, which is applied in fermentation and other directions, can solve the problems of slow reaction rate, low optical purity of products, and reduce the application scope of enzymatic kinetic resolution process, so as to achieve maximum application value and improve performance Effect

Inactive Publication Date: 2011-08-17
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are some shortcomings in this traditional secondary alcohol resolution method: in the resolution process, the donors used are generally relatively common vinyl acetate and isopropenyl acetate.
During their use, the reaction rate is often slow, and the optical purity of the obtained product is not high, which greatly reduces the application range of the enzymatic kinetic resolution process.

Method used

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  • Kinetic resolution method of secondary alcohol
  • Kinetic resolution method of secondary alcohol
  • Kinetic resolution method of secondary alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1) Add p-chlorophenol, propionic acid, dicyclohexylcarbodiimide and 4-dimethylaminopyridine with a molar ratio of 1:1:1:0.03, stir and react for 7 hours, filter, dry the filtrate, concentrate, pass column, obtain p-chlorophenyl propionate as an acyl donor for subsequent use;

[0023] 2) Add phenylethyl alcohol and p-chlorophenyl propionate at a molar ratio of 1:0.5 to 2 mL of toluene, react with 5 mg / mL Novozyme 435 for 3 hours at a reaction temperature of 30°C, and obtain a conversion rate of 50%, e.e. >99% esters.

Embodiment 2

[0025] 1) Add p-chlorophenol, n-butyric acid, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in a molar ratio of 1:2:2:0.05, stir for 3 hours, filter, dry the filtrate, concentrate, Go through the column to obtain p-chlorophenyl n-butyrate as an acyl donor for subsequent use;

[0026] 2) Add phenylethyl alcohol and p-chlorophenyl butyrate at a molar ratio of 1:3 to 6 mL of toluene, react with 20 mg / mL Novozyme 435 for 0.5 hours at a reaction temperature of 60°C, and obtain a conversion rate of 50%, e.e. >99% esters.

Embodiment 3

[0028] 1) Add p-chlorophenol, n-valeric acid, dicyclohexylcarbodiimide and 4-dimethylaminopyridine with a molar ratio of 1:1.5:1.5:0.05, stir and react for 6 hours, filter, dry the filtrate, concentrate, Go through the column to obtain p-chlorophenyl valerate as an acyl donor for subsequent use;

[0029] 2) Add phenylethyl alcohol and p-chlorophenyl valerate in a molar ratio of 1:2 to 2 mL of toluene, react with 10 mg / mL Novozyme 435 for 0.5 hours at a reaction temperature of 40°C, and obtain a conversion rate of 50%, e.e. >99% esters.

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Abstract

The invention discloses a secondary alcohol kinetic resolution method which comprises the following steps of: (1) adding parachlorophenol, organic acid, dicyclohexylcarbodiimide and 4- dimethylamino pyridine, the molar ratio of which is 1:1-2:1-2:0.03-0.05, stirring and reacting for 3 to 7 hours, filtrating, drying filtrate, concentrating and carrying out column chromatography so as to obtain pure ester being used as acyl donor for standby application; (2) adding secondary alcohol, acyl donor and 5 to20mg / mL lipase into 2-6mL of organic solvent, wherein the molar ratio between the secondary alcohol and the acyl donor is 1:0.5 to 3, reacting for 0.5 to 3 hours at the reaction temp[rapture of 30 to 60 DEG C so as to obtain ester with 50% conversion rate and 99% of e.e value. In the method, the conversion rate of the secondary alcohol reaches 50% in a very short time; the e.e value of the obtained ester reaches nearly 100%, properties of products is greatly increased, various requirements on purity can be met and very great application value is realized.

Description

field of invention [0001] The invention relates to a kinetic resolution method, in particular to a kinetic resolution method for secondary alcohols. Background technique [0002] Various monochiral secondary alcohols are very important chiral synthons, and are indispensable intermediates in the synthesis of medicines, agricultural chemicals, daily necessities, pheromones and high-quality liquid crystals, and are also important in asymmetric synthesis. chiral auxiliaries. Enzymatic kinetic resolution (Kinetic Resolution, KR) racemate is currently the preferred method for the preparation of monochiral secondary alcohols. However, this traditional secondary alcohol resolution method has certain shortcomings: in the resolution process, the donors used are generally relatively common vinyl acetate and isopropenyl acetate. During their use, the reaction rate is often slow, and the optical purity of the obtained product is not high, which greatly reduces the application range of ...

Claims

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Application Information

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IPC IPC(8): C12P41/00
Inventor 徐刚陈永军吴坚平杨立荣
Owner ZHEJIANG UNIV
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