Synthetic method of tazobactam diphenylmethyl ester

The technology of Zobactam diphenylmethyl ester and synthesis method is applied in the field of drug synthesis, which can solve the problems of many by-products, low product yield, environmental pollution, etc., and achieve the reduction of waste solid generation, simple post-processing operation, and improved The effect of purity

Inactive Publication Date: 2018-12-21
ASYMCHEM LAB TIANJIN
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0010] The main purpose of the present invention is to provide a kind of synthetic method of tazobactam diphenylmethyl ester, to solve the exi

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  • Synthetic method of tazobactam diphenylmethyl ester
  • Synthetic method of tazobactam diphenylmethyl ester
  • Synthetic method of tazobactam diphenylmethyl ester

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Example Embodiment

[0024] As described in the background art, the existing methods for synthesizing tazobactam diphenylmethyl ester have the problems of more by-products, low product yield and serious environmental pollution. In order to solve the above technical problems, this application provides a method for synthesizing tazobactam diphenylmethyl ester. The synthesis method includes: under the action of a catalyst, the compound A and hydrogen peroxide are oxidized to obtain tazobactam two Benzyl methyl ester, the synthetic route is as follows:

[0025]

[0026] In the above synthesis method, the tazobactam diphenylmethyl ester product is precipitated in a solid form, and the desired product can be obtained only by filtering after the reaction is completed. In the synthesis method provided in this application, hydrogen peroxide is used as the oxidant, and the only by-product is water. This aspect can greatly reduce the generation of waste and solid, and the amount of three wastes is greatly reduc...

Example Embodiment

[0038] Example 1

[0039]

[0040] At 20-25°C, compound A (10g, 23.0mmol) was placed in a 250mL four-necked flask, and then acetone (50mL) was added. The system was pale yellow and clear. The temperature of the above system is raised to 50℃, and the temperature is controlled at about 50℃, and then 35% hydrogen peroxide (6.70g, 69.0mmol) and Na are added to the above system 2 WO 4 .2H 2 O (0.152g, 0.46mmol), after dripping, continue to keep heat preservation and stirring, the system is milky white and turbid, HPLC tracks the reaction process until the raw material has been reacted.

[0041] After the reaction is completed, the product system is cooled to 20-25° C., and a 10 wt% sodium sulfite aqueous solution is added dropwise to the above system to quench the remaining hydrogen peroxide. Then the system was cooled to 0-5°C and filtered to obtain a white solid product of 9.67 g after drying, with a yield of 95.7% by weight and a purity of 98.1%.

[0042] The spectrum data of the whit...

Example Embodiment

[0043] Example 2

[0044] The difference from Example 1 is that the molar ratio of compound A and the hydrogen peroxide is 1:2.

[0045] The yield of tazobactam diphenylmethyl ester was 85.4 wt%, and the purity was 90.7%.

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Abstract

The invention provides a synthetic method of tazobactam diphenylmethyl ester. The synthetic method comprises the following step: under the action of a catalyst, a compound A and hydrogen peroxide aresubjected to an oxidation reaction to obtain the tazobactam diphenylmethyl ester (the synthetic route is as follows). In the synthetic method provided by the application, the hydrogen peroxide is usedas an oxidant, and the only by-product is water, so that on the one hand, the generation of waste solids can be greatly reduced, the amount of three wastes is greatly reduced, and the environment-friendly performance of the process is improved, and on the other hand, since the reaction by-product is only water, the synthetic method is adopted to facilitate improvement of the purity of a tazobactam diphenylmethyl ester product. Besides, the synthetic method has the advantages that the purity of the product can reach 98%, the post-treatment operation is simple, the separation yield is as high as 95.7%, and amplified production is easy.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing tazobactam diphenylmethyl ester. Background technique [0002] Tazobactam is a new penicillane sulfone β-lactamase inhibitor developed by Japan Dapeng Pharmaceutical Company. In 1992, the compound preparation of tazobactam sodium / piperacillin (1:8) was first launched in France for the treatment of various bacterial infections. Tazobactam has the characteristics of good stability, low toxicity and strong enzyme inhibitory activity, and is currently the most promising β-lactamase inhibitor in clinical evaluation. Due to the excellent properties of tazobactam, many scientific research institutes and manufacturers at home and abroad have conducted extensive research on its synthesis and achieved certain results. [0003] The existing literature reports that the key intermediate penicillanic acid diphenylmethyl ester-1α-oxide is prepared by diazotization, brom...

Claims

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Application Information

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IPC IPC(8): C07D499/87C07D499/04
CPCC07D499/04C07D499/87
Inventor 洪浩卢江平包登辉袁龙
Owner ASYMCHEM LAB TIANJIN
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