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Method for preparing bicalutamide from N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenylsulfenyl)-2-hydroxy-2-methyl-propanamide

A technology of trifluoromethylphenyl and hydroxypropionamide, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as high production cost, environmental pollution, and complicated treatment, and achieve low cost , Reduce environmental pollution, easy to react

Inactive Publication Date: 2012-02-15
宁波人健药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The post-treatment of this kind of oxidant is also complicated during oxidation, the production cost is relatively high, and the pollution to the environment cannot be ignored

Method used

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  • Method for preparing bicalutamide from N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenylsulfenyl)-2-hydroxy-2-methyl-propanamide
  • Method for preparing bicalutamide from N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenylsulfenyl)-2-hydroxy-2-methyl-propanamide
  • Method for preparing bicalutamide from N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenylsulfenyl)-2-hydroxy-2-methyl-propanamide

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Effect test

Embodiment 1

[0031] Compound 1 (10.0g, 0.025mol) was dissolved in acetone (30ml), sodium bicarbonate (0.1g, 0.00125mol) was added, and the reaction temperature was slowly added dropwise at 0°C with a concentration of 30% aqueous hydrogen peroxide ( 2.8g, 0.025mol), keep the temperature for 24h. The reaction solution was poured into water (100ml) and stirred for 30min. After filtration, the filter cake was washed with water, and air-dried at 50°C to obtain 4.1 g of white bicalutamide solid, with a yield of 38.2%, a melting point of 190-193°C, and an HPLC content of 97.8%.

Embodiment 2

[0033] Compound 1 (10.0g, 0.025mol) was dissolved in acetone (50ml), sodium bicarbonate (0.1g, 0.00125mol) was added, and the reaction temperature was slowly added dropwise at 0°C with a concentration of 30% aqueous hydrogen peroxide ( 2.8g, 0.025mol), keep the temperature for 24h. The reaction solution was poured into water (100ml) and stirred for 30min. After filtration, the filter cake was washed with water, and air-dried at 50°C to obtain 4.2 g of white bicalutamide solid, with a yield of 39.3%, a melting point of 190-193°C, and an HPLC content of 98.0%.

Embodiment 3

[0035] Compound 1 (10.0g, 0.025mol) was dissolved in acetone (80ml), sodium bicarbonate (0.1g, 0.00125mol) was added, and the reaction temperature was slowly added dropwise at 0°C with a concentration of 30% aqueous hydrogen peroxide ( 2.8g, 0.025mol), keep the temperature for 24h. The reaction solution was poured into water (100ml) and stirred for 30min. After filtration, the filter cake was washed with water, and air-dried at 50°C to obtain 3.8 g of white bicalutamide solid, with a yield of 35.3%, a melting point of 190-193°C, and an HPLC content of 98.7%.

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Abstract

The invention discloses a method for preparing bicalutamide from N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenylsulfenyl)-2-hydroxy-2-methyl-propanamide. The method adopts N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenylsulfenyl)-2-hydroxy-2-methyl-propanamide as a raw material, and comprises the following step that bicalutamide is obtained by an oxidation reaction in a solvent in the presence of an oxidizing agent. The method is characterized in that the oxidizing agent is a hydrogen peroxide aqueous solution and the solvent is added with sodium bicarbonate as a catalyst. Compared with the prior art, the method has the advantages that the oxidizing agent and the catalyst all have abundant sources in the market, are cheap and easily available and have low costs; reaction conditions are mild and waste capable of polluting the environment is not produced; and a heavy metal catalyst is not needed so that environmental pollution is reduced and environmental protection requirements are satisfied.

Description

technical field [0001] The invention relates to a preparation method of an antineoplastic drug bicalutamide. Background technique [0002] Bicalutamide, as a non-steroidal antiandrogen compound, can feedback-inhibit the secretion of gonadotropes from the anterior pituitary gland, which can reduce the production of androgen but has almost no androgen activity. Bicalutamide was successfully developed by British company Astra Zeneca and first launched in the UK in 1995. This drug is used to treat prostate cancer, and it is the most widely used antiandrogen drug. Prostate cancer has a high incidence worldwide and is the second leading cause of death among men. Inhibiting the level of androgen in the body is a common method for the treatment of prostate cancer. Bicalutamide has been widely used in the treatment of prostate cancer because of its strong efficacy, convenient administration and few side effects. [0003] Bicalutamide is produced by oxidation of a bicalutamide thi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/46C07C315/02
Inventor 顾华平郑飞
Owner 宁波人健药业集团股份有限公司
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