Synthesis method for dehydroepiandrosterone

A technology of dehydroepiandrosterone and a synthesis method, applied in the directions of steroids, organic chemistry, etc., can solve the problems of high risk, cumbersome post-processing process, difficult reaction control, etc., and achieves low price, simple post-processing process, The effect of easy control of reaction conditions

Inactive Publication Date: 2011-10-12
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The invention overcomes the shortcomings of the traditional production method, such as difficult reaction control, cumbersome post-treatment process, high risk, and environmental poll

Method used

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  • Synthesis method for dehydroepiandrosterone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] In a 1000-ml reaction flask equipped with a reflux tube and a thermometer, add 50 grams of gestational dienolone acetate and 400 mL of absolute ethanol (or 95% ethanol) and stir to dissolve, add 10.7 grams of hydroxylamine hydrochloride and 18.2 grams of dihydrate Sodium acetate was dissolved in 100 mL of aqueous solution, heated to reflux for 1 hour, cooled to room temperature, the reaction solution was slowly poured into 500 mL of ice water, a large amount of product precipitated, left standing for 1 hour, suction filtered, and dried to obtain 52 grams of the product.

[0015] Add 52 grams of acetic acid pregnant dienol ketoxime, 520 mL of dichloromethane (or toluene 600M1; or 450 mL of 1,2-dichloroethane) and 15.5 grams of triethylamine in a 1000 ml reaction bottle, stir at room temperature to dissolve, and cool down Add 29 g of p-toluenesulfonyl chloride (or 27.2 g of benzenesulfonyl chloride) and 17 mg of N,N-lutidine (DMAP) to -20°C, and react at -20°C for 1 hour. ...

Embodiment 2

[0018] In a 2000 ml reaction flask equipped with a reflux tube and a thermometer, add 100 grams of dienolone acetate and 800 mL of absolute ethanol (or 95% ethanol) and stir to dissolve, add 48 grams of hydroxylamine hydrochloride and 165 grams of dihydrate Sodium acetate was dissolved in 600mL of aqueous solution, heated to reflux for 5 hours, cooled to room temperature, the reaction solution was slowly poured into 14000mL of ice water, a large amount of product was precipitated, left standing for 2 hours, suction filtered, and dried to obtain 105 grams of the product.

[0019] Add 105 grams of acetic acid pregnant dienol ketoxime, 1050 mL of dichloromethane (or 1200 mL of toluene; or 900 mL of 1,2-dichloroethane) and 86 grams of triethylamine in a 2000 mL reaction bottle, stir and dissolve at room temperature, and cool down Add 108 g of p-toluenesulfonyl chloride (or 100 g of benzenesulfonyl chloride) and 3.5 g of N,N-lutidine (DMAP) to 25°C, and react at 25°C for 10 hours. ...

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Abstract

The invention belongs to a novel synthesis method for dehydroepiandrosterone, which comprises the following steps: oximation of 16-dehydropregnenolone acetate, Beckmann rearrangement, hydrolysis and refining to obtain a product. The synthesis method is characterized by carrying out oximation of ketone by using sodium acetate as a base and water and ethanol as solvent, carrying out Beckmann rearrangement, hydrolysis and one-pot refining reaction, reacting 16-dehydropregnenolone acetate oxime with p-toluenesulfonamide chloride, benzenesulfonyl chloride, triethylamine or N,N-dimethyl-pyridine (DMAP) in a dichloromethane solution, concentrating the solvent after reaction, adding methanol and a sodium hydroxide solution for refluxing hydrolysis, cooling and regulating the pH value to 7-8, adding activated carbon, then refluxing for 30-60 minutes, filtering, concentrating, crystallizing, and centrifuging to obtain the product. The synthesis method provided by the invention is simple to operate, and has characteristics of mild reaction conditions, high yield, low environmental pollution and the like.

Description

technical field [0001] The present invention specifically relates to a new synthetic method of dehydroepiandrosterone Background technique [0002] DHEA is an important physiologically active substance secreted by the human body. It has a wide range of physiological activities. It is a precursor of sex hormones and can prevent diabetes, obesity, anti-carcinogenic and viral infection, immune response and stress response. Relieve tension etc. Its clinical application is a hotspot in current research. There are already products on the market abroad, which are used in the treatment of systemic lupus erythematosus and anti-allergy / asthma. At present, DHEA is mainly obtained through chemical synthesis, biological synthesis and extraction from natural products. Biological synthesis and extraction from natural products have many problems such as low yield, cumbersome methods, high cost, and huge waste. Chemical synthesis methods mainly include, Wallis ES etc. use cholesterol and ...

Claims

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Application Information

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IPC IPC(8): C07J1/00
Inventor 申利群左前进雷福厚吴来喜黄素玉
Owner HUNAN KEREY BIOTECH
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