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Novel method for preparing 1-oxacephalosporin derivative

A technology of oxacephalosporins and manufacturing methods, applied in the new manufacturing field of 1-oxacephalosporin derivatives, which can solve the problems of low yield, high light and expensive photoreaction equipment, etc.

Inactive Publication Date: 2015-04-01
JEIL PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, illumination usually requires expensive photoreactive equipment
In the above method, in order to obtain a 7α-methoxy-3-chloromethyl compound from a 3-exomethylene compound, the intermediate is temporarily cut off and synthesized by reacting chlorine in the presence of quinoline as a base, but There is a defect of low yield

Method used

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  • Novel method for preparing 1-oxacephalosporin derivative
  • Novel method for preparing 1-oxacephalosporin derivative
  • Novel method for preparing 1-oxacephalosporin derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0081] [Example 1] (6R,7R)-7-(difluoromethylthio)acetamido)-3-(chloromethyl)-7-methoxy-8-oxo-5-oxo Production of diphenylmethyl hetero-1-aza-bicyclo[4,2,0]oct-2-ene-2-carboxylate

[0082] Step 1. (6R,7R)-7-(N-chloro-4-methylbenzamido)-3-(chloromethyl)-8-oxo-5-oxa-1-azabicyclo[ 4.2.0] Synthesis of oct-2-ene-2-carboxylic acid benzhydryl ester

[0083] A. Dichloromethane 1804mL, (6R,7R)-7-(4-methylbenzamido)-3-(chloromethyl)-8-oxo-5-oxa-1-aza- 180.4 g of diphenylmethyl bicyclo[4.2.0]oct-2-ene-2-carboxylate was charged into the reactor, and the reaction solution was cooled to 0°C. After adding 35.7 g of 2-picoline and cooling to -55°C, 122.7 g of trichloroisocyanuric acid was added dropwise. At this time, after the temperature of the reaction solution was reacted at -55±5°C for 30 minutes, the target compound, namely (6R,7R)-7-(N-chloro-4-methylbenzamido)-3- A solution of diphenylmethyl (chloromethyl)-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate.

[0084] B. Dichl...

Embodiment 2

[0099] [Example 2] (7R)-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-7-(4-methylbenzamido)-7-methyl Production of Diphenylmethyl Oxy-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate

[0100] Step 1. (6R,7R)-7-(N-chloro-4-methylbenzamido)-3-(chloromethyl)-8-oxo-5-oxa-1-azabicyclo[ 4.2.0] Synthesis of oct-2-ene-2-carboxylate diphenylmethyl ester

[0101] A. Dichloromethane 1804mL, (6R,7R)-7-(4-methylbenzamido)-3-(chloromethyl)-8-oxo-5-oxa-1-aza- 180.4 g of diphenylmethyl bicyclo[4.2.0]oct-2-ene-2-carboxylate was charged into the reactor, and the reaction solution was cooled to 0°C. After adding 35.7 g of 2-picoline and cooling to -55 degreeC, 122.7 g of trichloroisocyanuric acid was dripped. At this time, after the temperature of the reaction solution was reacted at -50±5°C for 30 minutes, the target compound, namely (6R,7R)-7-(N-chloro-4-methylbenzamido)-3- A solution of diphenylmethyl (chloromethyl)-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate.

[0102] B...

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Abstract

The present invention relates to a novel method for preparing a 1-oxacephalosporin derivative, which is an intermediate for the synthesis of 1-oxacephalosporin which is useful as an antibacterial agent. The preparation method of the present invention uses a simple halogenating agent to show remarkable stability, have a simple reaction process, allow a reaction to be readily controlled, and reduce reaction time, and thus is very efficient and improves the production yield of 1-oxacephalosporin which is useful as an antibacterial agent.

Description

technical field [0001] The present invention relates to a novel production method of a 1-oxacephalosporin derivative which is an intermediate for synthesizing 1-oxacephalosporin useful as an antibacterial agent. Background technique [0002] 1-oxacephalosporin 1-oxacephalosporin-7α-formazan is known as an important intermediate in industrially efficient production of 1-oxacephalosporins such as latacef or fluoxefe Oxy-3-chloromethyl derivatives. [0003] It is known that the manufacturing method is to irradiate the raw material 3-exomethylene compound with Cl 2 A method for 7α-methoxylation after addition. However, illumination usually requires expensive photoresponse equipment. In the above method, in order to obtain a 7α-methoxy-3-chloromethyl compound from a 3-exomethylene compound, the intermediate is temporarily cut off and synthesized by reacting chlorine in the presence of quinoline as a base, but There is the defect that the yield is low. Contents of the invent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D505/06A61K31/5365A61P31/04
CPCC07D501/57C07D505/06A61K31/5365A61P31/04
Inventor 李相均河弘柱秋素米安桢丌
Owner JEIL PHARM CO LTD
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