Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of 7-ADCA

A 7-ADCA and temperature control technology, applied in the direction of organic chemistry, etc., can solve the problems of low yield, many steps, and high requirements for reaction conditions, and achieve the effect of high yield, few operation steps, and high safety

Active Publication Date: 2014-09-24
江苏悦新药业有限公司 +1
View PDF3 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This step currently has problems such as high requirements for reaction conditions, many steps, and low yield.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of 7-ADCA
  • Preparation method of 7-ADCA

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 1. Oxidation

[0049] Dissolve 37.2g of penicillin G potassium in water, adjust the pH to about 3 with dilute sulfuric acid, slowly add 10.2g of 40% hydrogen peroxide dropwise, control the temperature at about 1-3°C, and control the reaction end point with thin-layer chromatography or HPLC. Add 2.0mol / L sulfuric acid after the reaction, when the reaction solution becomes white and turbid, add dilute sulfuric acid to pH 1.5, let it stand, filter, wash the filter cake with ice water, and dry it in vacuum to obtain 34.6g white powdery solid , yield 93%.

[0050] 2. Preparation of cephalosporin G

[0051] (1) Preparation of BSU

[0052] Using 500ml of toluene as solvent, add 31.5g of urea, 0.4g of saccharin, and distill at normal pressure. When the water content is controlled to 0.025%, add 116ml of hexamethyldisilazane, heat up and reflux, control the temperature at 110°C, and react for 4 hours , concentrated under normal pressure, and about 150ml of toluene was distill...

Embodiment 2

[0058] 1. Oxidation

[0059] Dissolve 55.4g of penicillin G potassium in water, adjust the pH to about 3 with dilute sulfuric acid, slowly add 13.85g of 40% hydrogen peroxide dropwise, control the temperature at 1-3°C, and control the reaction end point with thin-layer chromatography or HPLC. After the reaction, add 2.0mol / L sulfuric acid, when the reaction solution becomes white and turbid, add dilute sulfuric acid until the pH is 2, let it stand, filter, wash the filter cake with ice water, and dry it in vacuum to obtain 52.2g of white powdery solid , yield 94.2%.

[0060] 2. Preparation of cephalosporin G

[0061] (1) Preparation of BSU

[0062] Using 500ml of toluene as solvent, add 31.5g of urea, 0.315g of saccharin, and distill at normal pressure. When the water content is controlled to 0.02%, add 116ml of hexamethyldisilazane, heat up and reflux, control the temperature at 110°C, and react for 4 hours , concentrated under normal pressure, distilled off about 150ml of...

Embodiment 3

[0068] 1. Oxidation

[0069] Dissolve 37.2g of penicillin G potassium in water, adjust the pH to about 3 with dilute sulfuric acid, slowly add 11.16g of 40% hydrogen peroxide dropwise, control the temperature at 1-3°C, and control the reaction end point with thin-layer chromatography or HPLC. After the reaction, add 2.0mol / L sulfuric acid, when the reaction solution becomes white and turbid, add dilute sulfuric acid to pH 1.7, let it stand, filter, wash the filter cake with ice water, and dry it in vacuum to obtain 34.4g white powdery solid , yield 92.5%.

[0070] 2. Preparation of cephalosporin G

[0071] (1) Preparation of BSU

[0072] Using 500ml of toluene as solvent, add 31.5g of urea, 0.473g of saccharin, and distill at normal pressure. When the water content is controlled to 0.015%, add 116ml of hexamethyldisilazane, heat up and reflux, control the temperature at 110°C, and react for 4 hours , concentrated under normal pressure, and about 150ml of toluene was distill...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of 7-ADCA. The method includes the steps that penicillin G potassium salt serves as a raw material, hydrogen peroxide serves as an oxidizing agent, liquid BSU serves as a protective agent, a combination of pyridine hydrobromide and oxalic acid serves as a ring enlargement catalyst, and 7-ADCA is obtained through the steps of oxidization, ring enlargement, enzymolysis and the like. The method has the advantages that safety of the production process is high, production cost is low, emission of three wastes is small, operation steps are fewer, the yield is high, and quality is good.

Description

technical field [0001] The invention relates to a preparation method of a compound, especially a preparation method of 7-ADCA. Background technique [0002] 7-ADCA is an important intermediate of oral cephalosporins, mainly used in the synthesis of cephalexin, cefadroxil, cephradine and other antibiotics. The chemical name of 7-ADCA is 7-amino-3-desacetoxycephalosporanic acid, and its chemical structure is as follows: [0003] [0004] The chemical synthesis of 7-ADCA is widely used in industrial production and is currently a commonly used method. Patent CN101735246 and literature (Liu Dongzhi, Qu Hongmei, Zhang Tianyong. Synthesis progress of 7-ADCA [J] foreign medicine antibiotics volume, 1998,19 (4): 267-268.) disclose the basic process route of this method, namely Using penicillin G potassium salt as raw material, the reaction is completed in three steps, and the production process route is shown in the accompanying drawing. The first step is the oxidation of penic...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/18C07D501/04
CPCC07D501/04C07D501/18
Inventor 王菊明
Owner 江苏悦新药业有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com