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Method for preparing (1R, 4s)-(-)-2-azabicyclo[2,2,1]hepta-5-ene-3-one

An azabicyclo and formulation technology, applied in the direction of microorganism-based methods, biochemical equipment and methods, microorganisms, etc., can solve the problems of expensive finished drugs, expensive products, complicated production processes, etc., and achieve reaction and post-processing steps The effect of simplicity, ease of implementation, and low cost of raw materials

Active Publication Date: 2014-08-27
YINGKOU SANZHENG NEW TECH CHEM INDCO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the production process of biological enzyme bacteria used in the above-mentioned patents is complicated, and the product price is expensive, so that the price of finished medicine is expensive.
bring a great economic burden to consumers

Method used

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  • Method for preparing (1R, 4s)-(-)-2-azabicyclo[2,2,1]hepta-5-ene-3-one

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Embodiment

[0022] 1. Add 30g (±)-2-azabicyclo[2,2,1]hept-5-en-3-one to 260g (40mmol, PH=7.5) phosphate buffer solution, stir at room temperature until completely dissolved ; Then add 0.20g of biological enzyme --- Bacillus subtilis bacteria powder; stir and react at 20°C for 33 hours, during which time samples are taken for measurement, the final conversion rate of the reaction is ≥ 95%, and the ee value is ≥ 99.5%. Use 18% hydrochloric acid to adjust the pH value of the reaction solution to 7.01-7.02; filter the reaction solution, rinse the filter cake with water; combine the washing solution and the filtrate; extract the combined solution three times with 600g ethyl acetate; concentrate the oil layer; Add n-heptane into the kettle, heat the contents of the kettle, and stir at 80-85°C for 30 minutes; naturally cool to room temperature; filter the contents of the kettle and rinse the filter cake with 10g of n-heptane; vacuum-dry at 35-40°C The filter cake obtained 10.6 g of (1R,4S)-(-)-2...

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Abstract

The invention discloses a method for preparing (1R, 4s)-(-)-2-azabicyclo[2,2,1]hepta-5-ene-3-one, and relates to a method for preparing (1R, 4s)-(-)-2-azabicyclo[2,2,1]hepta-5-ene-3-one through bio-enzyme catalytic hydrolysis of racemized lactam, belonging to the field of biochemical engineering. The invention specifically relates to a method for biologically resolving the racemized lactam by use of a cheap bio-enzyme to obtain chiral (1R, 4s)-(-)-2-azabicyclo[2,2,1]hepta-5-ene-3-one. The reaction system is as follows: 10-100g of (+ / -)-2-azabicyclo[2,2,1]hepta-5-ene-3-one and 0.2-20g of bio-enzyme bacillus subtilis powder are added into 260g (40mmol, pH=7.0-7.5) of phosphate buffer solution respectively and react for 10-48 hours at 5-35 DEG C, wherein the conversion rate is greater than or equal to 90%, and the ee value of the product is greater than or equal to 99.5%. Since the cost of the bio-enzyme adopted in the method is only 1-3% of the selling price of the product, the method disclosed by the invention has great economy and technical feasibility. By adopting the method disclosed by the invention, the problems of high production cost and high product price of the existing preparation method are solved.

Description

technical field [0001] The invention relates to a method for preparing (1R,4S)-(-)-2-azabicyclo[2,2,1]hept-5-en-3-one by catalyzing the hydrolysis of racemic lactam by biological enzyme, belonging to field of biochemical engineering. technical background [0002] (1R,4S)-(-)-2-Azabicyclo[2,2,1]hept-5-en-3-one is the most important raw material or intermediate for the synthesis of anti-AIDS drug-abacavir One of the isomers, so (1R,4S)-(-)-2-azabicyclo[2,2,1]hept-5-ene-3- Ketones are economically attractive and promising. According to the report of UNAIDS, by 2015, the funds used for AIDS prevention and treatment in the world will reach 22.5 billion US dollars; it is expected that the funds used in this field will continue to grow in the future, so the market prospect is very bright. Although there are a variety of processes to synthesize the anti-AIDS drug-abacavir (abacavir), but with (1R,4S)-(-)-2-azabicyclo[2,2,1]hept-5-ene-3 - Ketone is used as an important raw materi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P17/10C12R1/125
Inventor 朱乃昌杨国民李成金贺从主潘立强刘翠袁媛
Owner YINGKOU SANZHENG NEW TECH CHEM INDCO