Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of preparation method of 17-iodo-androst-5,16-dien-3β-ol

A technology of androstane and diene, which is applied in androstane derivatives, chemical instruments and methods, steroids and other directions, can solve the problem of large amount of iodine element, and achieve easy acquisition, reduced impurity generation and low price. Effect

Inactive Publication Date: 2020-10-02
ZHEJIANG UNIV OF TECH +1
View PDF2 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of 17-iodo-androst-5,16-dien-3β-ol

Examples

Experimental program
Comparison scheme
Effect test

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%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com