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

Preparation method of 17,21-dihydroxy steroid derivative

A technology of bishydroxysteroid and steroid enol silyl ether, which is applied in the field of preparation of 17,21-bishydroxysteroid derivatives, can solve the problems of no literature report and the like, achieves simple operation, high yield and easy industrialization Effect

Active Publication Date: 2015-10-14
TIANJIN JINYAO GRP
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the enol silyl ether compound I shown in the following formula is the method for preparing the corresponding steroidal 17,21-dihydroxy compound as a starting material, and there is no literature report yet

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
  • Preparation method of 17,21-dihydroxy steroid derivative
  • Preparation method of 17,21-dihydroxy steroid derivative
  • Preparation method of 17,21-dihydroxy steroid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Preparation of 17,21-dihydroxy compound AIII with enol silicon ether compound AI as starting material

Embodiment 1-1

[0051] Take compound AI (100g, 0.23mol) and dissolve it in 1L dichloromethane solution; take mCPBA (85%, 162.4g, 0.8mol) and dissolve it in 3.25L dichloromethane solution and add powdery dry KHCO 3 (70g, 0.7mol); combine mCPBA and KHCO 3 The mixed solution was added to the dichloromethane solution of compound AI cooled to 0°C in 1 hour. The temperature of the reaction system was controlled to 0~5°C, and the reaction system was stirred while adding. Thin layer chromatography was used to monitor the progress of the reaction. After the reaction is complete, add an appropriate amount of 10% sodium thiosulfate aqueous solution to remove the excess mCPBA, use starch potassium iodide test paper to test the non-oxidation of the reaction solution, add 1L water, separate the layers, separate the organic layer, and use 1L dichloromethane for the water layer Extract once, combine the organic layers and wash with water to neutrality, concentrate and nearly dry to obtain crude AII. The crude A...

Embodiment 1-2

[0053] Take compound AI (100g, 0.23mol) and dissolve it in 1L dichloromethane solution; take mCPBA (85%, 162.4g, 0.8mol) and dissolve it in 3.25L dichloromethane solution and add powdered dry KHCO3 (70g, 0.7mol) ); put mCPBA and KHCO 3 The mixed solution was added to the dichloromethane solution of compound AI cooled to 10°C within 1 hour, and the temperature of the reaction system was controlled to 10°C±2°C. Stirring while adding, the progress of the reaction was monitored by thin layer chromatography After the reaction is complete, add an appropriate amount of 10% sodium thiosulfate aqueous solution to remove excess mCPBA, use starch potassium iodide test paper to test the non-oxidation of the reaction solution, add 1L of water, separate the layers, separate the organic layer, and use 1L of dichloride for the water layer. Methane was extracted once, the combined organic layer was washed with water to neutrality, concentrated to near dryness to obtain crude AII. The crude AII o...

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 relates to a method for preparing a 17,21-dihydroxy steroid compound by taking a steroid silyl enol ether compound I as an initiator.

Description

technical field [0001] This patent relates to a preparation method of 17,21-dihydroxy steroid derivatives. Background technique [0002] 17,21-dihydroxyl is an important functional group of steroidal compounds, and many steroidal compounds have the structure of 17,21-dihydroxyl or the corresponding ester, such as: dexamethasone, diflumethasone, betamethasone, prednisolone , prednisone, halometasone, methylprednisolone, aclomethasone, paramethasone, methylprednisolone acetate, loteprednol etabonate, etc. Therefore, the preparation of steroidal 17,21-dihydroxy compounds is very important. [0003] The document "J.Org.Chem.1986,51,4323-4325" reported that at 0°C, a dichloromethane solution of m-chloroperoxybenzoic acid (mCPBA, 3 equivalents) was slowly added dropwise to a steroid enol silicon Ether 14 (1 equiv) and KHCO 3 (Excessive) dichloromethane mixed solution, reacted for 1.5 hours, and then added 1N HCL / THF solution, a solid was precipitated, and the product cortisone ...

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
IPC IPC(8): C07J5/00C07J21/00
CPCC07J5/0076C07J21/00C07J71/0015
Inventor 卢彦昌张杰王淑丽
Owner TIANJIN JINYAO GRP
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