Preparation method of 7-phenylacetamido alkane acid

A technology of phenylacetamidoalkanoic acid and phosphate buffer solution, which can be used in fermentation and other directions, can solve problems such as high energy consumption, and achieve the effects of reduced energy consumption, obvious economic and social benefits, and simple post-processing.

Inactive Publication Date: 2017-02-15
SHAXING CHEM TAIZHOU CITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Involves freezing, high temperature and other operations, high energy consumption

Method used

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  • Preparation method of 7-phenylacetamido alkane acid

Examples

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Effect test

Embodiment 1

[0023] Preparation of 7-phenylacetamidoalkanoic acid

[0024] In the reactor, add concentration is 0.05mol / L, phosphate buffer solution 300g of pH=6, penicillin potassium salt 37.2g, immobilized chloroperoxidase (CPO) 0.005mmol, under stirring, heat up to 30 ℃, Add 4.1g of hydrogen peroxide (H2O2) dropwise, react for 1 hour, take a sample for testing, after the raw material point disappears, continue to stir for 2 hours, cool down to 10°C, separate the catalyst, adjust the pH of the reaction solution to about 4 with dilute hydrochloric acid, and then cool to 0~5°C, keep warm for 2 hours, filter with suction, rinse the filter cake with an appropriate amount of water, add an appropriate amount of methanol, drain, and dry in vacuum at 50°C to obtain 30.2g of white or off-white solid, content 98.5%, yield 90.5%.

Embodiment 2

[0026] Preparation of 7-phenylacetamidoalkanoic acid

[0027] Add 300 g of pH=6 concentration of 0.05 mol / L phosphate buffer solution, 37.2 g of penicillin potassium salt, and 0.005 mmol of immobilized chloroperoxidase (CPO) into the reactor. 10.8g of tert-butyl hydroperoxide (TBHP), react for 1 hour, take a sample for detection, after the raw material point disappears, continue to stir for 2 hours, cool down to 10°C, separate the catalyst, adjust the pH of the reaction solution to about 4 with dilute hydrochloric acid, and then cool Heat at 0-5°C, keep warm for 2 hours, filter with suction, rinse the filter cake with an appropriate amount of water, add an appropriate amount of methanol, drain, and dry in vacuum at 50°C to obtain 30.1 g of white or off-white solid with a content of 98%. The rate is 90.1%.

Embodiment 3

[0029] Preparation of 7-phenylacetamidoalkanoic acid

[0030] In the reactor, add 300 g of pH=6 concentration of 0.05 mol / L citrate buffer solution, 37.2 g of penicillin potassium salt, 0.005 mmol of immobilized chloroperoxidase (CPO), and, under stirring, heat up to 30° C., drop Add 6.8g of hydrogen peroxide (H2O2), react for 1 hour, take a sample for detection, after the raw material point disappears, continue to stir for 2 hours, cool down to 10°C, separate the catalyst, adjust the pH of the reaction solution to about 4 with dilute hydrochloric acid, and then cool it to 0 ~5°C, keep warm for 2 hours, filter with suction, rinse the filter cake with an appropriate amount of water, add an appropriate amount of methanol, drain, and dry in vacuum at 50°C to obtain 28.4g of a white or off-white solid with a content of 97.5% and a yield of 85%. %.

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Abstract

The invention relates to a preparation method of a compound intermediate, and specifically relates to a preparation method of 7-phenylacetamido alkane acid. According to the preparation method, penicillin potassium salts are taken as the raw material, and an enzyme catalyst and an oxidant are added into a solvent in sequence to carry out catalytic oxidation reactions to obtain 7-phenylacetamido alkane acid. In the conventional technology, there are multiple steps; while in the provided preparation method, there is only one step, so the total reaction time is shortened, and the energy consumption is largely reduced. The reactions are carried out at a room temperature or a temperature close to the room temperature; the reaction conditions are mild, the reaction time is short, the using amount of catalyst is little; the preparation method is environment-friendly and generates little pollution; moreover, the operation is simple, the cost is low, the yield can reach 90.0%, the purity can reach 98.0%; the product quality is good, prominent economic benefits and social benefits are generated, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a compound intermediate, in particular to a preparation method of 7-phenylacetamidoalkanoic acid. Background technique [0002] 7-amino-3-desacetoxy cephalosporanic acid (7-ADCA) is an important intermediate of semi-synthetic cephalosporins, and there are more than ten varieties of cephalosporins synthesized with it, while 7- Phenylacetaminoalkanoic acid is a key intermediate for the preparation of cephalosporin intermediate 7-ADCA, which is prepared from penicillin industrial salt. [0003] Most of the literature reports on the intermediates of 7-phenylacetamidoalkanoic acid are to obtain penicillin sulfoxide ester through esterification of penicillin sulfoxide, and then to obtain 7-phenylacetamidoalkanoic acid through catalytic ring expansion and hydrolysis. At present, hexamethyldisilazide (BSU) is widely used in industry as the carboxyl protecting agent in the synthesis process of 7-phenylacetamidoa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P35/00
CPCC12P35/00
Inventor 王文秀吴金跃
Owner SHAXING CHEM TAIZHOU CITY
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