Method for preparing cephalosporin intermediate 7-ADCA

A 7-ADCA and cephalosporin technology, applied in the field of compound preparation, can solve the problems of insufficient yield, poor quality, and low yield

Inactive Publication Date: 2010-06-16
杨石
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, in the industrial production of 7-ADCA in China, there are problems such as low yield, poor quality, and insufficient output.

Method used

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  • Method for preparing cephalosporin intermediate 7-ADCA
  • Method for preparing cephalosporin intermediate 7-ADCA
  • Method for preparing cephalosporin intermediate 7-ADCA

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The first step: the preparation of penicillin G sulfoxide (III)

[0024] 1. Preparation of Oxidant Peracetic Acid

[0025] Add 100g (1.67mol) of glacial acetic acid and 4.7g (0.047mol) of 98% concentrated sulfuric acid into the reactor, and slowly add 92.5g (0.82mol) of 30% hydrogen peroxide dropwise at 30 to 35°C under stirring. Stir at room temperature for 5h and store at low temperature.

[0026] 2. Oxidation process

[0027] Add 37.25g (0.1mol) of penicillin G potassium into the reactor, then add 25mL of water to dissolve it, cool it down to 0°C in an ice bath, measure 50g (0.1mol, C=15%) of peracetic acid, and add it to the reaction In the container (with a mechanical stirring device), use potassium acetate solid to adjust the PH process and carry out HPLC analysis by sampling every half an hour to track the reaction of raw materials. Precipitate, stand in an ice-water bath for 0.5h, filter, wash the filter cake with ice water, until Ba(NO 3 ) 2 Solution inspe...

Embodiment 2

[0043] The first step: the preparation of penicillin G sulfoxide (III)

[0044] 1. Preparation of Oxidant Peracetic Acid

[0045] Add 100g (1.67mol) of glacial acetic acid and 4.7g (0.047mol) of 98% concentrated sulfuric acid into the reactor, and slowly add 92.5g (0.82mol) of 30% hydrogen peroxide dropwise at 30 to 35°C under stirring. Stir at room temperature for 5h and store at low temperature.

[0046] 2. Oxidation process

[0047] Add 37.25g (0.1mol) of penicillin G potassium into the reactor, then add 25mL of water to dissolve it, cool it down to 0°C in an ice bath, measure 50g (0.1mol, C=15%) of peracetic acid, and add it to the reaction In the container (with a mechanical stirring device), use potassium acetate solid to adjust the PH process and carry out HPLC analysis by sampling every half an hour to track the reaction of raw materials. Precipitate, stand in an ice-water bath for 0.5h, filter, wash the filter cake with ice water, until Ba(NO 3 ) 2 Solution inspe...

Embodiment 3

[0063] The first step: the preparation of penicillin G sulfoxide (III)

[0064] 1. Preparation of Oxidant Peracetic Acid

[0065] Add 100g (1.67mol) of glacial acetic acid and 4.7g (0.047mol) of 98% concentrated sulfuric acid into the reactor, and slowly add 92.5g (0.82mol) of 30% hydrogen peroxide dropwise at 30 to 35°C under stirring. Stir at room temperature for 5h and store at low temperature.

[0066] 2. Oxidation process

[0067] Add 37.25g (0.1mol) of penicillin G potassium into the reactor, then add 25mL of water to dissolve it, cool it down to 0°C in an ice bath, measure 50g (0.1mol, C=15%) of peracetic acid, and add it to the reaction In the container (with a mechanical stirring device), use potassium acetate solid to adjust the PH process and carry out HPLC analysis by sampling every half an hour to track the reaction of raw materials. Precipitate, stand in an ice-water bath for 0.5h, filter, wash the filter cake with ice water, until Ba(NO 3 ) 2 Solution inspe...

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PUM

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Abstract

The invention discloses a method for preparing cephalosporin intermediate 7-ADCA. The preparation method has the advantages of high reaction yield and good quality. In the method, penicillin G sylvite is taken as a raw material and is oxidized into penicillin G sulfoxide by peracetic acid, wherein the mass yield reaches over 85 percent; hydrobromic acid-pyridinium is taken as a catalyst and bis(trimethylsily) urea is taken as a carboxyl protective reagent, and cephalosporin G acid is obtained through ring expansion and rearrangement, wherein the mass yield of a coarse product reaches 90 percent; and side chains are catalyzed and hydrolyzed by immobilized penicillin G acylase to prepare the 7-ADCA. On the basis of the penicillin G sylvite, the total mass yield reaches over 40 percent.

Description

technical field [0001] The present invention relates to a preparation method of a compound, especially a preparation method of a cephalosporin intermediate, specifically a preparation method of 7-ADCA. Background technique [0002] 7-ADCA, chemical name: 7-amino-3-desacetoxycephalosporanic acid. [0003] Its chemical structural formula is as follows: [0004] [0005] 7-ADCA is one of the three mother nuclei (6-APA, 7-ACA, 7-ADCA) of the β-lactam antibiotic industry chain, which can be used to synthesize more than a dozen cephalosporin antibiotic drugs. [0006] The conversion from cheap penicillin G potassium to 7-ADCA through ring expansion and rearrangement is a commonly used method at present. With the improvement of penicillin fermentation technology level in our country, the production cost has been continuously reduced, and the production capacity of penicillin has been continuously increased. It is worth paying attention to the development of new cephalosporin a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/18
Inventor 杨石
Owner 杨石
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