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

3alpha-hydroxyl-5alpha-cholanic acid synthesis method

A synthetic method and technology of cholanic acid, applied in the direction of steroids, organic chemistry, etc., to achieve the effect of cheap starting materials

Active Publication Date: 2019-01-04
HEZE RUIZHI TECH DEV
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the 3α-hydroxyl-5α-cholanic acid isomer of lithocholic acid can be applied to the synthesis of other similar steroidal compound derivatives, and the 3α-hydroxyl-5α-cholanic acid isomer of lithocholic acid has a significant effect on the synthesis of lithocholic acid. The safety of use is of great significance, but there are few reports about the synthesis method of 3α-hydroxyl-5α-cholanic acid in the prior art. Therefore, it is possible to design a method that can stably obtain 3α-hydroxyl-5α-cholanic acid The method of synthesis is very important

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
  • 3alpha-hydroxyl-5alpha-cholanic acid synthesis method
  • 3alpha-hydroxyl-5alpha-cholanic acid synthesis method
  • 3alpha-hydroxyl-5alpha-cholanic acid synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] One, the synthesis of formula (2) compound

[0039] Take 10 g of hyodeoxycholic acid (25.5 mmol), add 100 mL of methanol, then cool down to 5 °C, add 0.5 mL of concentrated sulfuric acid dropwise within about 10 min, stir until the solid dissolves, raise to 25 °C, and stir for 8 h , HPLC detection showed that the reaction was complete, then adding 100 mL of saturated sodium bicarbonate solution to quench the reaction, concentrating under reduced pressure, extracting with 150 mL of ethyl acetate, combining the organic phases, followed by 2*150 mL of saturated sodium bicarbonate, 3*100 Wash with mL of saturated brine, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 10.4 g of a white solid with a molar yield of 100%. 1 H-NMR (400 MHz, CDCl 3 / TMS): δ = 0.66 (3 H, s, 18-H), 0.94 (6 H, t, J = 1.4 Hz), 3.63 (1 H, m, 6α-H), 3.69 (3 H, s) , 4.07(1H, m, 3α-H).

[0040] Two, the synthesis of formula (3) compound

[0041] Take 10 g o...

Embodiment 2

[0048] One, the synthesis of formula (2) compound

[0049] Take 10 g of hyodeoxycholic acid, add 100 mL of methanol, then cool down to 0°C, add 0.5 mL of concentrated sulfuric acid drop by drop within about 10 min, stir until the solid dissolves, rise to 25°C, stir for 12 h, and detect the reaction by HPLC complete, then add 100 mL of saturated sodium bicarbonate solution to quench the reaction, concentrate under reduced pressure, extract with 150 mL of ethyl acetate, and wash the organic phase with 2*150 mL of saturated sodium bicarbonate and 3*100 mL of saturated brine, respectively. Dry over sodium sulfate, filter, and concentrate to obtain 10.0 g of white solid, with a molar yield of 96.6%.

[0050] Two, the synthesis of formula (3) compound

[0051] Take 10 g of the compound of formula (2), add 200 mL of dichloromethane, stir at room temperature to dissolve, add 16 g of oxidant PCC, react for 20 min after the dropwise addition, TLC detection shows that the reaction is co...

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 3alpha-hydroxyl-5alpha-cholanic acid synthesis method. The hyodeoxycholic acid is used as the starting material, a lithocholic acid isomer 3alpha-hydroxyl-5alpha-cholanic acid is generated through four steps of reactions, namely 24-carboxyl esterification, oxidation of 3alpha-OH and 6alpha-OH into carbonyl, selective reduction and Huang Minglong reaction, the blank in thefield of synthesis of the lithocholic acid isomer is filled, in addition, the method stably acquires the lithocholic acid isomer, namely the 3alpha-hydroxyl-5alpha-cholanic acid, wherein the total yield of the lithocholic acid isomer, namely the 3alpha-hydroxyl-5alpha-cholanic acid, is relatively high and reaches 47%.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of 3α-hydroxyl-5α-cholanic acid. Background technique [0002] Lithocholic acid, named 3α-hydroxy-5β-cholanic acid, is a bile acid present in the bile of humans, cattle, and rabbits, and gallstones of cattle and pigs. Studies have shown that it and its derivatives have various physiological functions. Activity, the effect of inhibiting tumors, such as selectively killing neuroma cells, but has almost no toxicity to normal cells; the change of its content has important reference value in the diagnosis of liver diseases. [0003] [0004] In 1946, Journal of Biological Chemistry, 1946, 162, 555-563 reported that deoxycholic acid was used as the starting material, after methylation, hydroxyl double protection, and then selective removal of 3-OH protecting group, hydrolysis, and hydrogenation through seven steps of reaction synthesis Lithocholic acid....

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 韩迎郭彩云刘彦丽王尤汉姚洪董超
Owner HEZE RUIZHI TECH DEV
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