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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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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 existing method for synthesizing tazobactam diphenylmethyl ester more by-products, low product yield and environmental pollution serious problem

Method used

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

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preparation example Construction

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

[0025]

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

Embodiment 1

[0039]

[0040] At 20-25°C, compound A (10 g, 23.0 mmol) was placed in a 250 mL four-necked flask, and then acetone (50 mL) was added, and the system became light yellow and clear. The above system was heated up to 50°C, and the temperature was controlled at about 50°C, and then 35% hydrogen peroxide (6.70g, 69.0mmol) and Na 2 WO 4 .2H 2 O (0.152g, 0.46mmol), continue to insulate and stir after dropping, the system is milky white and turbid, and HPLC tracks the reaction process until the reaction of the raw materials is completed.

[0041] After the reaction is completed, the temperature of the product system is lowered to 20-25° C., and 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 then filtered to obtain 9.67 g of a white solid product after drying, with a yield of 95.7 wt % and a purity of 98.1 %.

[0042] The spectral data of the white solid product is...

Embodiment 2

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

[0045] The yield of tazobactam diphenylmethyl ester was 85.4wt%, 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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