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17-Iodoandrosta-5,16-dien-3beta-ol preparation method

A technology of androstane and diene is applied in the directions of androstane derivatives, chemical instruments and methods, steroids, etc., which can solve the problem of large amount of iodine element, achieve simple operation, good industrial application prospects, and reduce the generation of impurities amount of effect

Inactive Publication Date: 2019-01-04
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to overcome the problem of large amount of iodine in the preparation process of 17-iodo-androst-5,16-dien-3β-ol, the present invention provides a more economical and efficient 17-iodo-androst-5,16- The preparation method of dien-3β-alcohol

Method used

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  • 17-Iodoandrosta-5,16-dien-3beta-ol preparation method

Examples

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example 1

[0021] Add 0.84g of simple iodine, dissolve in 80ml of anhydrous ether, cool down to 0°C, slowly add 0.89g of TCCA, add 1.95g of tetramethylguanidine dropwise at 0°C, stir evenly, start to dropwise add 1.02g of dehydrogenated form Androsterone-17-hydrazone tetrahydrofuran (35ml) solution, control the reaction temperature -5-5 ° C, after the dropwise addition, remove the ice bath, react at room temperature for 1 h, filter the reaction solution, concentrate the filtrate, and obtain the oil under nitrogen protection Heat at 90°C for 4 hours, add an appropriate amount of ethyl acetate to reflux, filter, wash the filtrate with dilute hydrochloric acid, saturated brine, and pure water, collect the organic layer, filter, and concentrate to obtain 1.30 g of a light yellow solid, ethanol: water = 2: 1. Recrystallized to obtain 1.10 g of off-white solid, namely steroidal iodide: 17-iodoandrost-5,16-dien-3β-ol, with a yield of 83%. Example two

example 2

[0022] Add 0.84g of elemental iodine, dissolve in 80ml of anhydrous ether, cool down to 0°C, slowly add 0.89g of TCCA, add 2.65g of MTBD dropwise at 0°C, stir evenly, start to add 1.03g of dehydroepiandrosterone-17 -Hydrazone tetrahydrofuran (35ml) solution, control the reaction temperature -5-5°C, after the dropwise addition, remove the ice bath, react at room temperature for 1h, filter the reaction solution, concentrate the filtrate, and heat the obtained oil at 90°C under nitrogen protection After 4 hours, add an appropriate amount of ethyl acetate to reflux, filter, and wash the filtrate with dilute hydrochloric acid, saturated brine, and pure water respectively, collect the organic layer, filter, and concentrate to obtain 1.20 g of a light yellow solid, recrystallized with ethanol:water=2:1, 0.99 g of an off-white solid was obtained, which was steroidal iodide: 17-iodoandrost-5,16-dien-3β-ol, with a yield of 75%.

example 3

[0024] Add 0.84g of simple iodine, dissolve in 80ml of anhydrous ether, cool down to 0°C, slowly add 0.90g of TCCA, control the temperature at 0°C, add 1.90g of DABCO dropwise, stir evenly, start to drop 1.02g of dehydroepiandrosterone-17 -Hydrazone tetrahydrofuran (35ml) solution, control the reaction temperature -5-5°C, after the dropwise addition, remove the ice bath, react at room temperature for 1h, filter the reaction solution, concentrate the filtrate, and heat the obtained oil at 90°C under nitrogen protection After 4 hours, add an appropriate amount of ethyl acetate to reflux, filter, and wash the filtrate with dilute hydrochloric acid, saturated brine, and pure water respectively, collect the organic layer, filter, and concentrate to obtain 1.26 g of a light yellow solid, recrystallized with ethanol:water=2:1, 1.06 g of off-white solid was obtained, namely steroidal iodide: 17-iodoandrost-5,16-dien-3β-ol, with a yield of 80%.

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Abstract

The invention discloses a 17-Iodoandrosta-5,16-dien-3beta-ol preparation method. The 17-Iodoandrosta-5,16-dien-3beta-ol preparation method takes dehydroeopiandrosterone-17-hydrazone, trichloroisocyanuric acid (TCCA), tetramethyl guanidine (TMG) and elemental iodine as raw materials to react at 0-90 DEG C with existence of solvent and then performing treatment to obtain the 17-Iodoandrosta-5,16-dien-3beta-ol. According to the 17-Iodoandrosta-5,16-dien-3beta-ol preparation method, the TCCA serves as oxidizing agent, the elemental iodine serves as iodinating agent, an oxidizing iodination methodis applied to iodinating dehydroeopiandrosterone-17-hydrazone, so that, compared with traditional methods, the 17-Iodoandrosta-5,16-dien-3beta-ol preparation method can reduce consumption of the elemental iodine by a half and is simple in operation of reaction processes and easy to control, thereby having a good industrialized application prospect.

Description

technical field [0001] The invention belongs to the technical field of medicine preparation, and in particular relates to a preparation method of 17-iodo-androst-5,16-dien-3β-ol. Background technique [0002] Abiraterone acetate is an oral androgen inhibitor, which can inhibit the CYP450c17 enzyme in the human body, thereby inhibiting the synthesis of androgen. Prostate cancer patients whose tumors are still growing after treatment or surgical resection provide a new and effective therapeutic approach, and 17-iodo-androst-5,16-dien-3β-ol is a key intermediate in the synthesis of abiraterone acetate. In existing reports, the synthesis method of 17-iodo-androst-5,16-dien-3β-ol is as follows: [0003] [0004] In this synthetic method, it is necessary to use twice the molar amount of iodine element of dehydroepiandrosterone 17-hydrazone to participate in the reaction, and about three-quarters of the iodine element is converted into the guanidinium salt of hydrogen iodide, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0003
Inventor 李景华毛煜鑫柯永新尉海锋谢晓强张德法
Owner ZHEJIANG UNIV OF TECH
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