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Method for preparing S-2-(4-nitrobenzophenone) oxirane

A technology of nitrophenyl and ethylene oxide, which is applied in the field of biocatalytic asymmetric preparation of pharmaceutical chiral intermediates, can solve the problems of difficult industrial production and environmental protection, low product yield, and high cost of preparation columns, achieving reduction Effects of acid-base consumption, high catalytic efficiency, strong enzyme stereoselectivity

Inactive Publication Date: 2014-03-12
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This reaction will generate a large number of other side reactions, the industrial production and environmental protection are difficult, the cost of the industrial chiral preparation column is high, and the product yield is low

Method used

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  • Method for preparing S-2-(4-nitrobenzophenone) oxirane
  • Method for preparing S-2-(4-nitrobenzophenone) oxirane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1 The chemical synthesis of racemate 2-bromo-1-(4-nitrophenyl)-ethanol and 2-(4-nitrophenyl)oxirane mixture

[0022] Dissolve 5g of racemate p-nitrobromoacetophenone and 1g of sodium borohydride in 50mL of methanol, stir with a stirring bar, react in an ice bath environment for 3h, add 50mL of water, and at the same time add 300mL of ethyl acetate Shake the ester in a separatory funnel, keep the organic phase, and wash the organic phase with MgSO 4 Dry, and spin dry with a rotary evaporator to obtain racemate 2-bromo-1-(4-nitrophenyl)-ethanol: racemate 2-(4-nitrophenyl)oxirane (7: 3) The solid of the mixture is 4 g.

Embodiment 2

[0023] Enzyme-catalyzed generation of embodiment 2S-2-(4-nitrophenyl)oxirane

[0024] Centrifuge 100mL of fermentation broth to obtain 1.5g of halohydrin dehalogenase wet body bacteria and add it to 1000mL of transformation liquid, which contains 4g / L of the above mixture, 100mL of N,N-dimethylformamide, and 900mL of phosphate buffer , pH8.0, react for 1h. Then add 100mL of fermentation broth, centrifuge to obtain 1.5g of epoxide hydrolase wet bacteria, react for 30min, and determine the reaction end point by GC gas phase detection. After the reaction, the concentration of S-2-(4-nitrophenyl)oxirane in the conversion solution was 1.3 g / L.

Embodiment 3

[0025] The separation and purification of embodiment 3S-2-(4-nitrophenyl) oxirane

[0026] The transformation solution was centrifuged at 4000 rpm for 15 minutes to remove the bacteria, and 100 mL of ethyl acetate was added to the supernatant to shake well, and the organic phase was retained, and 1.2 g of solid was obtained by rotary evaporation. The solid substance was passed through a silica gel column, and the target substance was eluted with a mixture of ethyl acetate:petroleum ether (1:7). The eluate was passed through a rotary evaporator to obtain 1.0 g of S-2-(4-nitrophenyl)oxirane solid with high purity.

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Abstract

The invention belongs to the technical field of bionts and relates to a method for preparing S-2-(4-nitrobenzophenone) oxirane. According to the method, a racemate para-nitro bromoacetophenone is used as a raw material, and the high-purity S-2-(4-nitrobenzophenone) oxirane is finally obtained through ultrafiltration and silicagel column screening by a chemical synthesis method under coupled enzymatic reaction. According to the method for preparing the S-2-(4-nitrobenzophenone) oxirane, the activity of enzyme is high, the time is short, the cost is low, the purity of the S-2-(4-nitrobenzophenone) oxirane is high, the reaction conditions are mild, and the method has extremely high industrial prospects.

Description

technical field [0001] The invention relates to a method for preparing S-2-(4-nitrophenyl)oxirane, which belongs to the technical field of biocatalytic asymmetric preparation of medical chiral intermediates. Background technique [0002] Optically pure epoxides, as important chiral building blocks in synthetic chemistry, can be further transformed into many biologically active compounds, such as leukotrienes, insect pheromones, steroids, adrenergic blocking agents, neuroprotective agents and HIV protease inhibitors, etc., have very broad application prospects in industries such as medicine, pesticides and cosmetics. [0003] At present, according to literature reports, the preparation methods of S-2-(4-nitrophenyl)oxirane mainly include chemical synthesis and biological enzymatic methods. The chemical synthesis method takes p-nitrobromoacetophenone (CAS: 99-81-0) as the substrate, sodium borohydride as the reducing agent, and reacts in an appropriate amount of methanol. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P17/02
Inventor 邬敏辰冯峰何瑶谭中标李剑芳
Owner JIANGNAN UNIV
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