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Method for synthesizing 7-phenylacetylaminodeacetoxycephalo G acid

A technology of acetoxy head and phenylacetamido, applied in the field of synthesizing 7-phenylacetamido deacetoxy cephalosporin G acid, can solve problems such as high energy consumption, and achieve the effects of reducing industrial costs, preventing bumping, and being simple to operate

Inactive Publication Date: 2012-08-01
YANAN BICON PHARMACEUTICAL LISTED COMPANY
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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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 60g of penicillin G sulfoxide and 535ml of toluene to the flask, raise the temperature to 42°C under stirring, and drop 120ml of trimethylbromosilane toluene solution into the flask at the same time while maintaining a constant speed (the amount of trimethylbromosilane is penicillin 1 times the molar weight of G sulfoxide) and 60ml of pyridine toluene solution (the amount of pyridine is 0.2 times the molar weight of penicillin G sulfoxide), drop them at the same time in about 1 hour, and raise the temperature to 50°C after the dropping, and keep it under vacuum After 1 hour, the temperature was raised to reflux for ring expansion. Finally obtain cephalosporin G acid 98g tidal product.

Embodiment 2

[0017] Add 60g of penicillin G sulfoxide and 535ml of toluene to the flask, raise the temperature to 40°C under stirring, and drop 80ml of trimethylbromosilane toluene solution into the flask at the same time while maintaining a constant speed (the amount of trimethylbromosilane is penicillin 0.5 times the molar weight of G sulfoxide) and 100ml of pyridine toluene solution (wherein the amount of pyridine is 0.3 times the molar weight of penicillin G sulfoxide), the two are dripped at the same time in about 45 minutes. Keep it for 1 hour, then raise the temperature to reflux and expand the ring. Finally obtain cephalosporin G acid 104g tide product.

Embodiment 3

[0019] Add 60g of penicillin G sulfoxide and 535ml of toluene to the flask, heat up to 40°C under stirring, and drop 150ml of trimethylbromosilane toluene solution into the flask at a constant speed (the amount of trimethylbromosilane is penicillin G 1 times the molar amount of sulfoxide), drop it in about 30 minutes, raise the temperature to 55 ° C after the drop, control the vacuum for half an hour, and after the heat preservation is over, add 50 ml of pyridine toluene solution dropwise while maintaining the vacuum (the amount of pyridine is the mole of penicillin G sulfoxide 0.1 times of the amount), the dropping time is about 2 hours. After the dropwise addition, the temperature was kept for 30 minutes, and finally the temperature was raised to reflux for ring expansion. Finally obtain cephalosporin 135g tide product.

[0020] Other embodiments: replace bromotrimethylsilane with trimethylchlorosilane, and replace organic base pyridine with 4-picoline, 2-picoline, triethyl...

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Abstract

The invention discloses a method for synthesizing 7-phenylacetylaminodeacetoxycephalo G acid. The method comprises the following step of: undergoing an esterification reaction on penicillin G sulfoxide in the presence of a trimethylhalosilane organic alkali to obtain a synthetic 7-phenylacetylaminodeacetoxycephalo G acid. The method is easy to operate, and is low in production cost.

Description

technical field [0001] The invention relates to a method for synthesizing 7-phenylacetylaminodesacetoxycephalosporin G. Background technique [0002] 7-Phenylacetylaminodesacetoxy cephalosporin G acid (referred to as cephalosporin G acid) is an important intermediate cephalosporin drug, which is prepared from penicillin industrial salt. [0003] Most of the intermediate bibliographical reports of cephalosporin G are that penicillin sulfoxide is esterified to obtain penicillin sulfoxide ester, and then cephalosporin G acid is obtained through catalyzed ring expansion hydrolysis. At present, hexamethyldisiloxane (BSU) is widely used in the industry as a carboxyl protecting agent in the synthesis of cephalosporin G. The ring expansion catalyst mainly uses pyridinium hydrobromide double salt, and the adding time is mainly after the end of esterification. [0004] The BSU synthesis route is to react trimethylchlorosilane with ammonia to obtain hexamethyldisilazane, and then ado...

Claims

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Application Information

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IPC IPC(8): C07D501/10C07D501/22
Inventor 周新基夏俊维陈新建李珣珣赵新峰
Owner YANAN BICON PHARMACEUTICAL LISTED COMPANY
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