Preparation method of progesterone carboxylate

The technology of progesterone and carboxylic acid is applied in the field of preparation of steroid drug intermediates, can solve the problems of low cost, large pollution, long route of carboxylate progesterone, etc., and achieves short synthesis time, high purity yield and abundant resources Effect

Inactive Publication Date: 2015-11-25
湖北竹溪人福药业有限责任公司
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problems of long synthesis route, high cost and heavy pollution of carboxylated progesterone from dienolone acetate, the present invention proposes a preparation method of carboxylated progesterone, which has rich raw material resources, short synthetic route and low 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
  • Preparation method of progesterone carboxylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) Cyanide

[0019] Under nitrogen protection, 20g of compound II, namely 4-androstenedione, and 40g of potassium tert-butoxide were added to 800g of ethylene glycol dimethyl ether and 240g of tert-butanol, and cooled to -10°C with stirring; slowly added 30g p-Toluenesulfonylmethyl isocyanide was added, the temperature was raised to 20 °C, stirred for 4 h, TLC until the reaction of the raw materials was complete; the ice water was separated out, and suction filtered to obtain an off-white solid, washed with water until neutral, and dried at 55 °C until At constant weight, 18 g of compound III, 3-oxo-4-ene-17-cyano, were obtained.

[0020] (2) Carboxylation

[0021] 18g of compound III, namely 3-oxo-4-ene-17-cyano, was added to the reaction flask, 144g of 50% sulfuric acid solution was added, the temperature was controlled to 50°C for the reaction, and TLC was monitored until the reaction of the raw materials was complete; Washed with a large amount of water until neu...

Embodiment 2

[0023] (1) Cyanide

[0024] Under nitrogen protection, 20 g of compound II, namely 4-androstenedione, and 60 g of potassium tert-butoxide were added to 900 g of ethylene glycol dimethyl ether and 300 g of tert-butanol, cooled to 0 °C with stirring, and 40 g of tert-butanol was slowly added. Methylbenzenesulfonylmethyl isocyanide, after the addition was completed, the temperature was raised to 25 °C, stirred for 3 h, TLC until the reaction of the raw materials was complete; the ice water was separated out, and the off-white solid was obtained by suction filtration, washed with water until neutral, and dried at 60 °C to constant 18.2 g of compound III, 3-oxo-4-en-17-cyano, were obtained.

[0025] (2) Carboxylation

[0026] 18.2g of compound III, namely 3-oxo-4-ene-17-cyano, was added to the reaction flask, 182g of 50% sulfuric acid solution was added, the temperature was controlled to 60°C for reaction, TLC was monitored until the reaction of the raw materials was complete, 364...

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 preparation method of progesterone carboxylate, which comprises the following step: by using a compound II 4-androstenedione as the raw material, carrying out cyanation and carboxylation to obtain the compound I progesterone carboxylate. The reaction is disclosed in the specification. By using the raw material 4-androstenedione with better price advantage, the method has the advantages of short synthesis route, low cost and high product yield. The product compound I progesterone carboxylate has the advantages of short synthesis time and high purity and yield of the synthesized intermediate; the HPLC (high performance liquid chromatography) is greater than or equal to 98%; and the total yield is greater than or equal to 95%. By using the compound II 4-androstenedione as the raw material, the method has the characteristics of more abundant resources and lower cost.

Description

technical field [0001] The invention relates to a preparation method of a steroid drug intermediate, in particular to a preparation method of a carboxylate progesterone. Background technique [0002] Progesterone carboxylate, chemical name: 3-oxo-androst-4-ene-17B-carboxylic acid. English name: 4-Androsten-3-one-5-ene-17-carboxylicacid; Molecular formula: C20H28O3; Molecular weight: 316.44. It is an important intermediate for the synthesis of steroid hormone raw materials. Domestic manufacturers generally use dienolone acetate as raw material to synthesize compound I, carboxyprogesterone, through five steps of hydrogenation, hydrolysis, esterification, oxidation and hydrolysis. The synthetic route is as follows: [0003] . [0004] The above-mentioned route utilizes dienolone acetate to synthesize carboxyprogesterone with long route, high cost and large pollution. Therefore, it is very important to develop a process for carboxylate progesterone with abundant raw materi...

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): C07J3/00
CPCC07J3/005
Inventor 周建生郑承刚杨艳青郑建雄侯海波刘林代先华
Owner 湖北竹溪人福药业有限责任公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap