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A kind of method adopting biological enzyme to catalyze the stereoselective resolution of loxoprofen enantiomer

A stereoselective, enantiomeric technology, applied in the field of loxoprofen enantiomers, can solve the problems of low reaction concentration, slow reaction rate, low optical purity of the product, etc., and achieves high reaction concentration, easy operation, and improved optical The effect of purity

Active Publication Date: 2021-11-05
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is, aiming at the difficult problems such as low product optical purity, low reaction concentration and slow reaction rate of chiral enantiomers separated by other racemate resolution methods, a method for obtaining partial configuration loxoprofen is proposed. enantiomeric approach

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] 100 mmol / L of racemic loxoprofen enantiomer and 100 mmol / L n-hexanol, 300 mg of Novozym ® Add 40086 lipase to 2 mL of organic solvent; heat the reaction in a 25 mL reaction tube at 400 rpm and 79 °C for 4 h. At this time, the substrate conversion rate was 52.34%, the enantiomeric excess value of the remaining loxoprofen enantiomer was 84.84%, and the target enantiomer yield was 88.09%.

Embodiment 2

[0016] Add 100 mmol / L of racemic loxoprofen enantiomer and 100 mmol / L n-hexanol, 300 mg of Novozym® 40086 lipase, 250 mg of anhydrous magnesium sulfate into 2 mL of organic solvent; The reaction tube was heated at 400 rpm and the reaction temperature was 79°C for 15 h in a mL reaction tube. At this point, the substrate conversion rate was 54.22%, the enantiomeric excess value of the remaining loxoprofen enantiomer was 90.94%, and the target enantiomer yield was 87.41%.

Embodiment 3

[0018] Add 300 mmol / L of loxoprofen enantiomers and 500 mmol / L n-hexanol, 300 mg of Novozym® 40086 lipase, 250 mg of anhydrous magnesium sulfate into 2 mL of organic solvent; in a 25 mL reaction tube The reaction was heated at 400 rpm and the reaction temperature was 79°C for 12 h. At this point, the substrate conversion rate was 59.91%, the enantiomeric excess value of the remaining loxoprofen enantiomer was 97.48%, and the target enantiomer yield was 79.17%.

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Abstract

This patent introduces a chiral resolution method for obtaining (RR)- and (SR)-loxoprofen enantiomers, that is, an enzymatic stereoselective esterification method for splitting loxoprofen partial enantiomers The invention belongs to the technical field of splitting chiral compounds by biological methods. Choose Novozym from Rhizomucor miehei ® 40086 lipase is used as a biocatalyst, and the lipase has the characteristics of high selectivity and high catalytic efficiency in the catalytic esterification of loxoprofen, and can obtain (RR)-loxoprofen and (SR) with high optical purity ‑Loxoprofen. After enzyme-catalyzed stereoselective esterification resolution, the enantiomeric excess value of the target product reached 98.64%, the yield was 72.70%, and the overall conversion rate of the substrate was 63.40%. Compared with other methods, the method has high reaction concentration, fast reaction rate, high optical purity of the product, simple operation and post-treatment, low cost, and green and environment-friendly production process, and is an efficient resolution method for loxoprofen.

Description

technical field [0001] The invention belongs to the preparation of chiral compounds by biological methods, and relates to an application of immobilized enzyme Novozym ® 40086 Stereoselective catalytic esterification of racemic loxoprofen to obtain two configurations of loxoprofen enantiomers. Using Novozym ® 40086 lipase selectively catalyzes esterification of racemic loxoprofen to (RS)- and (SS)-loxoprofen n-hexyl ester to obtain (RR)- and (SR)-loxoprofen with higher optical purity Loffin. Background technique [0002] Loxoprofen sodium is a non-steroidal anti-inflammatory analgesic drug (NSAIDs), developed and marketed by Japan Sankyo Co., Ltd. It is widely praised for its good analgesic effect, quick onset and small side effects. Loxoprofen is a chiral drug containing 4 enantiomers. The enantiomers of different configurations have different pharmacological activities. medicine. It is of great significance to develop a method for obtaining the single enantiomer of lo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P41/00C12P7/40
CPCC12P7/40C12P41/001
Inventor 唐课文张盼良袁欣许卫凤
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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