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Preparation technologies of tazobactam acid and tazobactam diphenylmethyl ester and application

A technology of diphenylmethyl zobactam acid and tazobactam acid, which is applied in the field of organic polymer synthesis technology, can solve problems such as low yield, achieve the effects of reducing production costs, reducing toxicity and harm, and increasing sales profits

Inactive Publication Date: 2018-06-15
常州红太阳药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In recent years, the international demand for tazobactam has been increasing, and the market prospect is very broad. More and more laboratories and companies have begun to study tazobactam; Synthetic method, using 6-APA as raw material, the key intermediate 6,6-dihydropenicillane sulfoxide diphenylmethyl ester is obtained through continuous reactions such as esterification, oxidation, and reductive debromination without separation, and then combined with 2 -Triphenylsilane-1,2,3-triazole reaction introduces the triazole ring, and the final product tazobactam is obtained through potassium permanganate oxidation and intermediate cresol deprotection; although this preparation method is compared to the existing Made of advanced technology, it is safer and more environmentally friendly, but the average final yield is about 70%-80%, and the yield is low

Method used

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  • Preparation technologies of tazobactam acid and tazobactam diphenylmethyl ester and application
  • Preparation technologies of tazobactam acid and tazobactam diphenylmethyl ester and application
  • Preparation technologies of tazobactam acid and tazobactam diphenylmethyl ester and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] The preparation process flowchart of tazobactamic acid, such as figure 1 As shown, it mainly includes the following steps:

[0068] Step 1: ring-opening reaction;

[0069] Step 2: chlorination reaction;

[0070] Step 3: condensation reaction;

[0071] Step 4: double oxidation reaction.

[0072] The reaction equation for the ring-opening reaction is as follows:

[0073]

[0074] The preparation steps are as follows:

[0075] Step 1.1: Put 3.0 parts of toluene, 0.2 parts of debrominated product and 0.1 part of MBT into reaction vessel A, heat up to 70°C and react for 80-100 minutes;

[0076] Step 1.2: After the reaction is completed, cool down to 58°C;

[0077] Step 1.3: Concentrate the product in step 1.2 to dryness under reduced pressure, add 2.3 parts of dichloromethane and stir until completely dissolved to obtain a clear liquid, and obtain a dichloromethane solution of the ring-opener.

[0078] The reaction equation of the chlorination reaction is as follow...

Embodiment 2

[0101] Step 1: Ring Opening Reaction

[0102] Step 1.1: Put 3.5 parts of toluene, 0.4 part of debrominated product and 0.2 part of MBT into reaction vessel A, heat up to 70-75°C and react for 80-100 minutes;

[0103] Step 1.2: After the reaction is completed, cool down to 75°C;

[0104] Step 1.3: Concentrate the product in step 1.2 to dryness under reduced pressure, add 2.5 parts of dichloromethane and stir until completely dissolved to obtain a clear liquid, and obtain a dichloromethane solution of the ring-opener;

[0105] Step 2: Chlorination reaction

[0106] Step 2.1: Transfer the dichloromethane solution of the ring-opening product in step 1.3 to the reaction vessel B, continuously stir and lower the temperature so that the dichloromethane solution of the ring-opening product in the reaction vessel B reaches 0-5°C;

[0107] Step 2.2: Slowly add 0.5 part of hydrochloric acid solution with a concentration of 31% to the reaction vessel B, and the dropping temperature is l...

Embodiment 3

[0123] Step 1: Ring Opening Reaction

[0124] Step 1.1: Put 3.2 parts of toluene, 0.25 parts of debrominated product and 0.14 parts of MBT into reaction vessel A, heat up to 70-75°C and react for 80-100 minutes;

[0125] Step 1.2: After the reaction is completed, cool down to 65°C;

[0126] Step 1.3: Concentrate the product in step 1.2 to dryness under reduced pressure, add 2.37 parts of dichloromethane and stir until completely dissolved to obtain a clear liquid, and obtain a dichloromethane solution of the ring-opener;

[0127] Step 2: Chlorination reaction

[0128] Step 2.1: Transfer the dichloromethane solution of the ring-opening product in step 1.3 to the reaction vessel B, continuously stir and lower the temperature so that the dichloromethane solution of the ring-opening product in the reaction vessel B reaches 0-5°C;

[0129] Step 2.2: Slowly add 0.37 parts of hydrochloric acid solution with a concentration of 31% to the reaction vessel B, and the dropping temperature...

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Abstract

The invention relates to preparation technologies of tazobactam acid and tazobactam diphenylmethyl ester and application. A preparation route is as follows: with methylbenzene, 2-mercaptobenzothiazoleand a debrominated product as starting materials, the tazobactam diphenylmethyl ester is prepared after a ring opening reaction, a chlorination reaction, a condensation reaction and a double oxidation reaction, then the tazobactam diphenylmethyl ester is transformed into the tazobactam acid after a deprotection reaction; a preparation method in the scheme is improved on the basis of an iodinationreaction in the prior art, and the chlorination reaction is introduced, so that the reaction quality is optimized, the product purity is improved, and use of toxic, harmful, flammable and explosive substances in the reaction process is reduced, and thus the reaction is more environment-friendly; the product yield can be as high as 98-99.92%, and the preparation cost is also lower than that of thepreparation technology in the prior art.

Description

technical field [0001] The invention relates to an organic polymer synthesis process, in particular to a preparation process and application of tazobactam acid and tazobactam diphenylmethyl ester. Background technique [0002] β-lactam antibiotics have a history of more than half a century since their birth. During this period, as bacteria continue to develop resistance to commonly used antibiotics, people continue to develop more efficient and more effective antibiotics against resistant bacteria, and at the same time produce β-lactamases that inactivate β-lactamases against resistant bacteria. The mechanism of -lactamase has developed a β-lactamase inhibitor that is used in combination with antibiotics, and the typical one is tazobactam. Tazobactam is also very effective on various types of β-lactamase and even type I enzymes, its effect is 10 times stronger than that of sulbactam, and its stability is better than that of clavulanic acid. The inhibitory effect of amidase...

Claims

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Application Information

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IPC IPC(8): C07D499/87C07D499/04A61K31/431A61P31/04
CPCC07D499/87A61K31/431C07D499/04
Inventor 陈建林张雪皎
Owner 常州红太阳药业有限公司
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