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

Synthesis method of intermediate 7-ketolithocholic acid of ursodeoxycholic acid

A technology of ursodeoxycholic acid and its synthesis method, which is applied in the field of organic chemical synthesis, and can solve the problems of high equipment requirements, unsuitability for large-scale production, and low yield.

Inactive Publication Date: 2017-08-01
EAST CHINA NORMAL UNIV
View PDF7 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method needs to use the high-temperature Huangminglong reaction in the process of preparing 7-ketolithocholic acid, which has higher requirements on equipment, low yield (58.94%), and is not suitable for large-scale production. The reaction formula is as follows:

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
  • Synthesis method of intermediate 7-ketolithocholic acid of ursodeoxycholic acid
  • Synthesis method of intermediate 7-ketolithocholic acid of ursodeoxycholic acid
  • Synthesis method of intermediate 7-ketolithocholic acid of ursodeoxycholic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] 1. Synthesis of the compound of formula (2): Dissolve cholic acid (9g, 22.0mmol) in 200mL of acetone / water (v / v=3:1), protect from light, slowly add NBS (5.7g, 31.9mmol), Reaction at room temperature 25°C for 2h. After the TLC detection reaction is complete, add 100mL saturated sodium bisulfite solution to quench the reaction, concentrate under reduced pressure until a white solid appears, and stop when poured into 1L of water, and a large amount of white solid is precipitated, left to stand for crystallization, filtered and dried to obtain the formula (2) Compound (8.5g white solid, yield 95%).

[0105]

[0106] 2. Synthesis of the compound of formula (3): Dissolve the compound of formula (2) (8.5g, 20.8mmol) in 100mL of DMF, add potassium carbonate (3.4g, 24.96mmol), heat up to 100°C, stir for ten minutes, add bromide Benzyl (2.7mL, 22.88mmol), reacted for 2h. After the reaction was detected by TLC, water (300 mL) was added and stirred, and the aqueous phase was ...

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 chemical synthesis method of intermediate 7-ketolithocholic acid (3alpha-hydroxy-7-one-5beta-cholestan-2-4-acid) of ursodeoxycholic acid, and belongs to the field of organic chemical synthesis. According to the method, cholic acid is adopted as a material, and is subjected to reactions including selective oxidation of 7alpha-hydroxy, benzyl esterification of a side chain carboxyl group, esterification of 3alpha-hydroxy, methanesulfonic acid esterification of 12alpha-hydroxy, elimination, hydrogenation and hydrolysis to synthesize the intermediate 7-ketolithocholic acid of the ursodeoxycholic acid; the cheap cholic acid is adopted as the material, the synthesis method has the advantages of being novel, low in cost, high in yield and environment-friendly and industrial production is facilitated.

Description

technical field [0001] The invention relates to a chemical synthesis method of 7-ketolithocholic acid (3α-hydroxy-7-keto-5β-cholestane-24-acid), an intermediate of ursodeoxycholic acid, belonging to the field of organic chemical synthesis. Background technique [0002] Ursodeoxycholic acid Ursodeoxycholic acid (UDCA), the chemical name is 3a, 7β-dihydroxy-5β-cholestane-24-acid, is the main active ingredient of the precious traditional Chinese medicine bear bile, bile acid in the human body under physiological conditions about 3%. Ursodeoxycholic acid can promote the secretion of endogenous bile acids and reduce reabsorption; antagonize the cytotoxicity of hydrophobic bile acids, protect liver cell membranes; dissolve cholesterol gallstones, and have immunomodulatory effects, approved by the FDA for Drugs for the treatment of cholestatic liver disease are commonly used drugs for liver protection and anti-inflammation. The traditional Chinese medicine bear bile powder is mad...

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 Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/005
Inventor 仇文卫
Owner EAST CHINA NORMAL UNIV
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