Dynamic kinetic method for resolving secondary alcohol

A dynamic kinetics, secondary alcohol technology, applied in fermentation and other directions, can solve the problems of reduced optical purity and high theoretical yield of products, and achieve great application value and improve performance.

Inactive Publication Date: 2011-07-20
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this traditional enzymatic kinetic resolution has a very important limitation: for a single enantiomer, the theoretical yield is only 50%.

Method used

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  • Dynamic kinetic method for resolving secondary alcohol
  • Dynamic kinetic method for resolving secondary alcohol
  • Dynamic kinetic method for resolving secondary alcohol

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0022] Example 1

[0023] 1) adding p-chlorophenol, n-valeric acid, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in a molar ratio of 1:1:1:0.03, stirring and reacting for 7 hours, filtering, drying the filtrate, and concentrating, Cross the column to obtain p-chlorophenyl n-valerate as the acyl donor for subsequent use;

[0024] 2) in 2mL of toluene, add phenethyl alcohol and p-chlorophenyl n-valerate in a molar ratio of 1:1, add 10mg / mLCD8604 and 5 mg / mL Novozyme 435 to react for 12 hours, and the reaction temperature is 30° C. to obtain a transformation efficiency. 100% ester with e.e value > 99%.

Example Embodiment

[0025] Example 2

[0026] 1) adding p-chlorophenol, n-valeric acid, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in a molar ratio of 1:2:2:0.05, stirring and reacting for 3 hours, filtering, drying the filtrate, and concentrating, Cross the column to obtain p-chlorophenyl n-valerate as the acyl donor for subsequent use;

[0027] 2) in the toluene of 6mL, add phenylethyl alcohol and p-chlorophenyl n-valerate that the molar ratio is 1:6, add 40mg / mLCD550 and 20mg / mL Novozyme 435 and react for 6 hours, and the reaction temperature is 60 ℃, and obtains transformation efficiency. 100% ester with e.e value > 99%.

Example Embodiment

[0028] Example 3

[0029] 1) add p-chlorophenol, n-hexanoic acid, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in a molar ratio of 1:1.5:1.5:0.05, stir and react for 6 hours, filter, dry the filtrate, concentrate, pass Column, obtain p-chlorophenyl n-hexanoate for subsequent use as acyl donor;

[0030] 2) in 2mL of toluene, add phenethyl alcohol and p-chlorophenyl n-hexanoate with a molar ratio of 1:3, add 20mg / mLCD8604 and 15 mg / mL Novozyme 435 to react for 6 hours, and the reaction temperature is 40° C. to obtain the transformation efficiency. 100% ester with e.e value > 99%.

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Abstract

The invention discloses a dynamic kinetic method for resolving secondary alcohol,Which comprises the following steps: (1) adding parachlorophenol, long-chain organic acid, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in a mol ratio of 1:(1-2):(1-2):(0.03-0.05), stirring to react for 3-7 hours, filtering, drying the filtrate, concentrating, and passing through columns to obtain a pure ester as an acyl donor for later use; and (2) adding secondary alcohol and the acyl donor in a mol ratio of 1:(1-6), 10-40mg/ml racemization catalyst and 5-20mg/ml lipase into 2-6ml of organic solvent, reacting at 30-60 DEG C for 6-12 hours to obtain the ester of which the conversion rate is 100% and the e.e value is greater than 99%. The invention overcomes the defects in the past dynamic kinetic resolution process; when the conversion rate of the secondary alcohol reaches 100%, the e.e value of the obtained ester can also approach to 100%; and the invention greatly enhances the properties of the product, can satisfy various requirements for purity, and has a high application value.

Description

Field of Invention [0001] The invention relates to a dynamic kinetic resolution method, in particular to a dynamic kinetic resolution method of a secondary alcohol. Background technique [0002] Various single-chiral secondary alcohols are very important chiral synthons, indispensable intermediates for the synthesis of medicines, agricultural chemicals, daily necessities, pheromones and high-quality liquid crystals, and are also important in asymmetric synthesis. chiral auxiliaries. The use of enzymatic kinetic resolution (Kinetic Resolution, KR) racemates is currently the preferred method for the preparation of single chiral secondary alcohols. However, this traditional enzymatic kinetic resolution has an important limitation: for a single enantiomer, the theoretical yield is only up to 50%. The dynamic kinetic resolution of secondary alcohols provides a new idea for obtaining single chiral secondary alcohols. Dynamic kinetic resolution (DKR) means that the resolution pr...

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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