Synthesis method of alkyl acid testosterone

A synthesis method and technology of alkyl acid, applied in the field of synthesis of alkyl acid testosterone, can solve the problems of large environmental pollution, many by-products, low yield, etc., and achieve the effects of low price, stable market supply, and reduced production cost

Active Publication Date: 2020-11-27
ZHEJIANG SHENZHOU PHARMA
View PDF9 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the limitations of large environmental pollution, many by-products and low yield in the existing process, and make the process more in line with the needs of industrial production, the invention provides a testosterone alkylate with low pollution, less impurity content and obvious economic benefits. resolve resolution

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 alkyl acid testosterone
  • Synthesis method of alkyl acid testosterone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis of embodiment 1 testosterone propionate

[0034] 1) Under the protection of nitrogen, put 10g of 4-androstenedione into 5ml of anhydrous methanol, add 3.82ml of trimethyl orthoformate, 0.1g of pyridinium p-toluenesulfonate, and keep warm at 20°C for reaction. After the reaction is completed, add 0.1ml of triethylamine was concentrated and filtered to obtain 10.2g of 3-methoxy-androst-3,5-dien-17-one.

[0035] 2) Put 10.2g of 3-methoxy-androst-3,5-dien-17-one into 10.2ml of methanol, add 0.1ml of pyridine, 1g of sodium borohydride, keep warm at 40°C, after the reaction is completed, water analysis, filtration, and drying to obtain 10.1g of 17β-hydroxyl-3-methoxyl-androst-3,5-diene

[0036] 3) Under nitrogen protection, put 10.1g of 17β-hydroxy-3-methoxy-androst-3,5-diene into 101ml of dichloromethane, add 0.01g of 4-dimethylaminopyridine, 5g of N,N - Diisopropylcarbodiimide (DIC), start stirring, add 12.1g propionic acid, keep warm at 5°C until complete r...

Embodiment 2

[0037] The synthesis of embodiment 2 testosterone enanthate

[0038] 1) Under the protection of argon, put 10g of 4-androstenedione into 100ml of absolute ethanol, add 17.4ml of triethyl orthoformate, 0.5g of pyridine hydrochloride, and keep warm at 40°C for reaction. After the reaction is completed, add 0.5 ml of triethylamine, concentrated and filtered to obtain 10.5 g of 3-ethoxy-androst-3,5-dien-17-one.

[0039] 2) Put 10.5g of 3-ethoxy-androst-3,5-dien-17-one into 52.5ml of ethanol, add 31.5ml of pyridine, 10.5g of potassium borohydride, and keep warm at 60°C. After the reaction is completed, Water analysis, filtration, and drying to obtain 10.4 g of 17β-hydroxy-3-ethoxy-androsta-3,5-diene

[0040] 3) Put 10.4g of 17β-hydroxy-3-ethoxy-androst-3,5-diene into 52ml of tetrahydrofuran, add 10.4ml of 20% dilute hydrochloric acid, keep warm at 20-30°C, after the reaction is completed, oxidize Sodium solution neutralization, concentration, water analysis, filtration, and dryin...

Embodiment 3 10

[0043] The synthesis of embodiment 3 testosterone undecanoate

[0044] 1) Under the protection of argon, put 10g of 4-androstenedione into 50ml of tetrahydrofuran, add 29.1ml of triethyl orthoformate, 1g of pyridinium hydrobromide, and keep warm at 50°C for reaction. After the reaction is completed, add 3ml of pyridine, Concentrate and filter to obtain 10.6 g of 3-ethoxy-androst-3,5-dien-17-one.

[0045] 2) Put 10.6g of 3-ethoxy-androst-3,5-dien-17-one into 106ml of tetrahydrofuran, add 10.6ml of triethylamine, 31.8g of sodium borohydride, keep warm at 20°C, and wait until the reaction is completed , water analysis, filtration, and drying to obtain 10.5g of 17β-hydroxy-3-ethoxy-androsta-3,5-diene

[0046] 3) Put 10.5g of 17β-hydroxy-3-ethoxy-androst-3,5-diene into 31.5ml of butanol, add 5.3ml of 20% dilute hydrochloric acid, keep warm at 20-30°C, after the reaction is completed, Neutralize with sodium hydroxide solution, concentrate, water analysis, filter, and dry to obtain...

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 synthesis method of alkyl acid testosterone, and belongs to the technical field of synthesis and processing of medicines. The method comprises the following steps of: taking4-androstenedione (4AD) as an initial raw material, firstly, carrying out enol ether protection on the keto group at the site 3, and reducing carbonyl at the site 17 into hydroxyl; or taking 4-androstenedione (4AD) as an initial raw material, firstly carrying out enol ether protection on the keto group at the site 3, then reducing carbonyl at the site 17 into hydroxyl, then carrying out hydrolysison the site 3 to obtain testosterone, and carrying out esterification and third-site hydrolysis to obtain the testosterone ester after testosterone third-site ketal protection. According to the method disclosed by the invention, the third site is protected during esterification reaction, the generation of impurities can be reduced, and an esterification reaction solvent is a water-insoluble organic solvent, so that after the reaction is completed, products can be directly extracted in a layered manner, a large amount of water does not need to be added to separate out the products, the amountof wastewater is reduced, the solvent can be recycled, and the process is more suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of synthesis and processing of medicines, in particular to a synthesis method of testosterone alkylate. Background technique [0002] Testosterone is a male hormone drug, which can promote the development and maturation of male sexual organs and secondary sexual characteristics, and can resist estrogen, and promote protein and bone synthesis. Testosterone is used to treat hypogonadism, to supplement the symptoms of insufficient autogenous secretion or the inability to naturally secrete testosterone, so testosterone can be supplemented regularly to maintain the content of testosterone in the blood. [0003] At present, most of the methods for synthesizing testosterone derivatives are synthesized by the acid chloride method, such as the synthetic method disclosed in the patent CN105732754A, which uses alcoholic hydroxy steroids as a starting material, uses a water-soluble organic solvent as a solvent, and adds...

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): C07J1/00
CPCC07J1/0025Y02P20/55
Inventor 黄橙橙邵振平王友富王荣王炳乾王洪福雷灵芝
Owner ZHEJIANG SHENZHOU PHARMA
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