Enzymatic resolution method of dl 1-phenylethanol compounds

A technology for phenylethanol and compounds, which is applied in the field of enzymatic splitting of racemic 1-phenylethanol compounds, can solve the problems of low yield, unsuitable for large-scale production, etc., and achieves environmental friendliness and great implementation value. and social benefits, the effect of high yield

Inactive Publication Date: 2009-08-12
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the presence of noble metal catalysts and t

Method used

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  • Enzymatic resolution method of dl 1-phenylethanol compounds
  • Enzymatic resolution method of dl 1-phenylethanol compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0127] In the reactor, it is 24.4 (0.02mol) g, 0.5g of biological enzyme, 51.6g (0.6mol) of vinyl acetate and 50ml of solvent cyclohexane to drop into the racemic 1-phenylethanol feeding amount successively, and the enzyme used is lipase AYS "Amano".

[0128] In a 250ml three-necked flask equipped with a thermometer, drying tube, and magnetic stirring, add 24.4g (0.2mol) of 1-phenylethyl alcohol, 8.6g (0.1mol) of vinyl acetate, 50ml of cyclohexane, and 0.5g of biological enzyme, After the addition, the temperature was fixed at 30°C, and the reaction was carried out for 5 hours. During the period, TLC plate monitoring or gas chromatography monitoring was completed. After the reaction was completed, the organic solvent and unreacted vinyl acetate were evaporated, and the residual liquid was separated to obtain colorless R- 1-phenylethyl alcohol acetate liquid and colorless S-(+)-1-phenylethyl alcohol liquid.

[0129] R-1-phenylethanol acetate was hydrolyzed with 5 mol / L NaOH so...

Embodiment 2

[0132] The feed amount of racemic 1-phenylethanol is 24.4g (0.2mol), biological enzyme 0.5g, vinyl acetate 86g (1mol) into the reactor successively, and the enzyme used is esterase XL23.

[0133] After the addition was complete, the temperature was fixed at 30° C., monitored by TLC plate or gas chromatography during the period, and the reaction time was 36 hours.

[0134] Other operations were the same as in Example 1 to obtain colorless S-(-)-1-phenylethanol and R-(+)-1-phenylethanol.

[0135] S-(-)-1-phenylethanol, yield 26%, ee value 96%; R-(+)-1-phenylethanol, yield 34%, ee value 98%. The boiling point is 87-89°C / 10mm Hg, and the melting point is 8-11°C.

Embodiment 3

[0137] The amount of feeding of racemic 1-phenylethanol is 24.4g (0.2mol) into the reactor successively, the biological enzyme used is 0.5g, vinyl acetate 172g (2mol), the used enzyme is esterase XL23 and esterase XL6 and the mass ratio of the two is 1:3.

[0138] After the addition was complete, the temperature was fixed at 40° C., monitored by TLC plate or gas chromatography during the period, and the reaction time was 72 hours.

[0139] Other operations were the same as in Example 1 to obtain colorless S-(-)-1-phenylethanol and R-(+)-1-phenylethanol.

[0140] S-(-)-1-phenylethanol, yield 46%, ee value 98%; R-(+)-1-phenylethanol, yield 49%, ee value 99%. The boiling point is 87-89°C / 10mm Hg, and the melting point is 8-11°C.

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Abstract

The invention relates to a method for separating a raceme based on a biological enzyme, in particular to an enzymatic separation method for racemizing 1-phenylethanol compound. The technical proposal adopted in the invention is that: the enzymatic separation method for racemizing the 1-phenyl ethanol compound comprises the following steps that: the vinyl acetate used as a raw material is reacted in organic solvent under the action of the biological enzyme to prepare an R-(+)-1-phenyl ethanol compound and an S-(-)-1-phenyl ethanol compound, and the reaction formula is shown as a top right formula, wherein R is one of or the combination of two or three of hydrogen, p-halogen, o-halogen, m-halogen, p-CN, o-CN, m-CN, p-C1 to C5 alkyl groups, o-C1 to C5 alkyl groups, m-C1 to C5 alkyl groups, p-nitro group, o-nitro group, m-nitro group, p-CF3,o-CF3 and m-CF3.

Description

technical field [0001] The invention relates to a method for splitting racemates based on biological enzymes, in particular to an enzyme splitting method for racemic 1-phenylethanol compounds. Background technique [0002] Chiral monomers R-(+)-1-phenylethanol compounds and S-(-)-1-phenylethanol compounds are an important chemical intermediate and pharmaceutical intermediate, usually used as an intermediate in organic synthesis of drugs body. In recent years, it has received more and more attention in agriculture, pharmaceutical industry and spice production. There are many methods for preparing R-(+)-1-phenylethanol compounds and S-(-)-1-phenylethanol compounds by splitting racemate 1-phenylethanol have been disclosed and some patents have been applied for. Patent PL194403 utilizes the broken tissue of celery (Apium graveolens) root to react in a buffer solution, and obtains R-(+)-1-phenylethanol and 29% by-product acetophenone, but does not obtain S-(-)-1- phenethyl alc...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P7/22
Inventor 于洪巍王博汤晓玲刘击
Owner ZHEJIANG UNIV
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