Process for preparing (R)-2-methylbutanoic acid and (R)-2-methylbutanoic acid ethyl ester via lipase resolution

A kind of technology of ethyl methyl butyrate and methyl butyric acid, applied in the field of biological separation of racemic compounds

Active Publication Date: 2010-04-14
JIANGNAN UNIV
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  • Abstract
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Problems solved by technology

On the other hand, most of the current enzymatic resolution research reports are mainly aimed at the resolution of (S)-type ethyl 2-methyl...

Method used

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Embodiment 1

[0033] Take 2.0mmol (R, S)-2-methylbutyric acid ethyl ester and place in 10mL 0.05mol / L KH2 PO 4 / K 2 HPO 4 10 g / L Rhizopuschinensis CCTCC M201021 lipase (RCL) was added to a ground-necked Erlenmeyer flask of buffer solution (pH 7.5), and the reaction was shaken at 200 r / min at 4°C. After 84 hours, the mixture was centrifuged, and the supernatant was extracted with ethyl acetate to extract the product and substrate, and the product and substrate were analyzed by chiral gas chromatography. The optical purity of the remaining substrate (R)-2-methylbutyric acid ethyl ester was 95.0%. rate 24.6%.

[0034] Product separation: In the hydrolysis split reaction system, the lipase is centrifuged from the reaction solution, the supernatant is extracted with n-heptane, and the extracted heptane phase is extracted with saturated NaHCO 3 Solution extraction, the obtained upper organic phase was separated using a silica gel column, and the solvent heptane was eluted with pentane, and the...

Embodiment 2

[0038] Take 2.0mmol (R, S)-2-methylbutyric acid ethyl ester and place in 10mL 0.05mol / L KH 2 PO 4 / K 2 HPO 4 20 g / L Candida rugosa lipase (CRL) was added to a ground-necked Erlenmeyer flask of buffer solution (pH 7.0), and the reaction was shaken at 45° C. at 200 r / min. After 12 hours, the mixture was centrifuged, and the supernatant was extracted with ethyl acetate to extract the product and substrate. The product and substrate were analyzed by chiral gas chromatography. The optical purity of the remaining substrate (R)-ethyl 2-methylbutyrate was 85.5%. rate of 14.5%.

[0039] Product separation: In the hydrolysis split reaction system, the lipase is centrifuged from the reaction solution, the supernatant is extracted with n-heptane, and the extracted heptane phase is extracted with saturated NaHCO 3 Solution extraction, the obtained upper organic phase was separated using a silica gel column, and the solvent heptane was eluted with pentane, and the target product (R)-2-m...

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Abstract

A process for preparing (R)-2-methylbutanoic acid and (R)-2-methylbutanoic acid ethyl ester via lipase resolution belongs to the technical field of resolution of racemic compounds by a biological method. The process of the invention includes two steps: the first step is to realize resolution of (R)-2-methylbutanoic acid ethyl ester via selective hydrolysis reaction catalyzed by lipase, and a second step includes utilizing (R)-2-methylbutanoic acid ethyl ester which is residual substrate obtained in the first step to perform a second selective hydrolysis reaction catalyzed by the lipase to realize resolution of the (R)-2-methylbutanoic acid, thereby finally obtaining the (R)-2-methylbutanoic acid ethyl ester with ee value of 95.0% and the (R)-2-methylbutanoic acid with ee value of 92.2%, and realizing resolution of the (R)-2-methylbutanoic acid and the (R)-2-methylbutanoic acid ethyl ester thereof which is difficult in resolution by the biological method and is seldom researched.

Description

technical field [0001] A kind of lipase resolution preparation (R)-2-methylbutyric acid and (R)-2-methylbutyric acid ethyl ester, involves Rhizopus chinensis (Rhizopus chinensis) CCTCC M201021 lipase catalysis with independent intellectual property rights ( The separation technology of (R)-2-methylbutyric acid ethyl ester and (R)-2-methylbutyric acid belongs to the technical field of biological separation of racemic compounds. Background technique [0002] 2-Methylbutyric acid and its short-chain esters are typical important chiral flavor substances with apple, strawberry and pineapple flavors, and different enantiomers correspond to different flavors and applications. In addition, 2-methylalkanoic acid with high optical purity can also be used as a valuable synthetic intermediate for the synthesis of many optically pure compounds such as biological pheromones. Therefore their split has aroused widespread interest. [0003] Compared with other resolution methods, lipase-ca...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P7/62C12P7/40
Inventor 王栋徐岩李小路
Owner JIANGNAN UNIV
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