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

Synthetic method of 3-keto-4-androstene-17β carboxylic acid and its methyl ester

A synthesis method and technology of methyl carboxylate, applied in the field of drug synthesis, can solve the problems of reduced molecular weight, low labor cost, inadequate environmental protection supervision, etc., and achieve the effects of reducing reaction steps, changing synthesis routes, and facilitating industrialized implementation.

Active Publication Date: 2016-12-07
HUNAN KEREY BIOTECH
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Before the end of the 1990s, due to the low labor cost in China and inadequate environmental protection supervision, the cost of planting turmeric to extract saponin was low, and the price of saponin was below 200,000 yuan / ton. With the increase of environmental protection costs, the current price of saponin is more than 800,000 yuan / ton. In addition, the synthesis of various steroidal compounds from saponin generally takes longer steps, and basically the molecular weight is greatly reduced. Therefore, the yield lower cost

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
  • Synthetic method of 3-keto-4-androstene-17β carboxylic acid and its methyl ester
  • Synthetic method of 3-keto-4-androstene-17β carboxylic acid and its methyl ester
  • Synthetic method of 3-keto-4-androstene-17β carboxylic acid and its methyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] This embodiment is a synthetic method of 3-keto-4-androstene-17β carboxylic acid, which specifically includes the following steps:

[0040] (1) Synthesis of Compound 04

[0041] Add 28g of testosterone and 500mL of anhydrous ether into a 1000mL reaction bottle, then cool down to 0°C, slowly add 12g of thionyl chloride dropwise, and continue the reaction for 5 hours after the dropwise addition. Then it was raised to room temperature overnight. After the reaction was completed, the solvent was spin-dried to obtain 28.28 g of yellow compound 04 with a molar yield of 94.90%.

[0042] (2) Synthesis of Compound 05

[0043] At room temperature, add 500ml tetrahydrofuran and 100ml triethyl orthoformate to a 1000ml reaction glass reaction bottle, stir, add PTS.H 2 O 0.5 g, Compound 04 100 g. Control the temperature at 40°C for 4 hours, spot the plate until the basic reaction is complete; cool down to room temperature, add 1ml of triethylamine, stir for 30 minutes, slowly pour...

Embodiment 2

[0049] This embodiment is a synthetic method of methyl 3-keto-4-androstene-17β carboxylate, and the difference from Example 1 is only that step (3) (c) is different, and (c) of this embodiment is specifically:

[0050] Add compound 05 to the Grignard reagent slowly dropwise into dimethyl carbonate solution (toluene 200ml, add dimethyl carbonate 33g), keep the reaction at 20°C for 4 hours, and spot the plate until the reaction is complete. Slowly add the reaction solution into glacial acetic acid solution (tap water 1000ml + glacial acetic acid 25ml), stop cooling down, concentrate at normal pressure, after concentrating toluene, drop to below 40°C (preferably 30-40°C), filter, wash with water until neutral, Drained and dried to obtain 89.66 g of methyl 3-keto-4-androstene-17β carboxylate, with a molar yield of 90.88%.

Embodiment 3

[0052] The difference between this embodiment and Example 1 is that the amount of thionyl chloride in step (1) is different. In this embodiment, the amount of thionyl chloride is 13g, and finally obtains the yellow compound 0428.09g, and the molar yield is 94.27%.

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 synthesis methods of 4-androsten-3-one-17-beta-carboxylic acid and methyl 4-androsten-3-one-17-beta-carboxylate. Cheap testosterone as a raw material undergoes a chlorination reaction, the reaction product is subjected to etherification protection and the branched chain at the 17 site of androstane is modified by a Grignard addition method so that 4-androsten-3-one-17-beta-carboxylic acid and methyl 4-androsten-3-one-17-beta-carboxylate are synthesized. The synthesis methods have the advantages of novel and short processes, high yield, economical efficiency, environmental friendliness and industrialization feasibility.

Description

technical field [0001] The invention relates to a method for synthesizing medicines, in particular to a method for synthesizing 3-keto-4-androstene-17β carboxylic acid and its methyl ester. Background technique [0002] Finasteride and Dutasteride are drugs for the treatment of benign prostatic hyperplasia and alopecia developed by Merck and Glaxo, respectively, with definite curative effects and few side effects. The traditional synthetic method of its important intermediate 3-keto-4-androstene-17β carboxylic acid and its methyl ester is to use turmeric extract saponin as raw material, and obtain through multi-step reaction (references: Journal of Chinese Pharmaceutical Sciences 2007 (16 )233–235; Fine ChemicalsVol.20.No.50 May 2003 307-309), the general reaction formula is as follows: [0003] [0004] Before the end of the 1990s, due to the low labor cost in China and inadequate environmental protection supervision, the cost of planting turmeric to extract saponin was...

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): C07J3/00
CPCC07J3/005
Inventor 左前进甘红星谢来宾
Owner HUNAN KEREY BIOTECH
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