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Preparation method of dehydroisoandrosterone

A technology for dehydroepiandrosterone and ketal compounds, which is applied in the field of preparation of dehydroepiandrosterone, can solve the problems of only 70% yield, temperature sensitivity, and difficulty in control, and achieves simple post-processing process and easy reaction conditions. Controlled, high-yield effects

Active Publication Date: 2012-07-25
湖南成大生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Acetic anhydride, acetone and two solvents and water are used in large amounts; the products of each step are sensitive to temperature, difficult to control, and the yield is only 70%

Method used

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  • Preparation method of dehydroisoandrosterone
  • Preparation method of dehydroisoandrosterone
  • Preparation method of dehydroisoandrosterone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Esterification reaction

[0036] Preparation of esterified product 3: Add 10 grams of compound 2 and 350 ml of acetic anhydride into the reactor under nitrogen protection, dissolve the system under stirring, then add 6 grams of p-toluenesulfonic acid at 20° C. ℃-25℃ for 5 hours, TLC detects that about 1%-2% of the raw materials are left, then control the temperature below 5℃ and slowly pour the system into 200 ml of ice water, stir at 0-5℃ for 2 hours, 0- Stand at 5°C for 2 hours, filter, wash with a large amount of water until neutral, and dry in vacuum at 40°C for 24 hours to obtain 10.74 g of white or off-white solid, with a mass yield of 107.4%.

[0037] Ketal reaction

[0038] Preparation of ketal 4: Add 20 grams of esterified product, 100 ml of ethylene glycol, and 100 ml of triethyl orthoformate into the reaction flask in sequence under nitrogen protection, and stir at 20°C for 10 minutes, and the system becomes turbid. Finally, add 0.13 g of p-toluenesulfonic ...

Embodiment 2

[0044] Preparation of esterified product 3: Add 10 grams of compound 2 and 150 ml of acetic anhydride into the reactor under nitrogen protection, dissolve the system under stirring, then add 7 grams of p-toluenesulfonic acid at 20°C under temperature control, and add 7 grams of p-toluenesulfonic acid at 20 ℃-25℃ for 5 hours, TLC detects that about 1%-2% of the raw materials are left, then control the temperature below 5℃, slowly pour the system into 200 ml of ice water, stir at 0-5℃ for 2 hours, 0- Stand at 5°C for 2 hours, filter, wash with a large amount of water until neutral, and dry in vacuum at 40°C for 24 hours to obtain 10.87 g of white or off-white solid, with a mass yield of 108.7%.

[0045] Preparation of ketal 4: Add 19.95 g of esterified product, 60 ml of ethylene glycol, and 70 ml of triethyl orthoformate into the reaction flask in sequence under nitrogen protection, and stir at 20°C for 10 minutes, and the system becomes turbid. Finally, add 0.2 gram of p-toluen...

Embodiment 3

[0049] Preparation of esterified product 3: Add 10 grams of compound 2 and 400 ml of acetic anhydride into the reactor under nitrogen protection, dissolve the system under stirring, then add 4.5 grams of p-toluenesulfonic acid at 20° C. ℃-25℃ for 5 hours, TLC detects that about 1%-2% of the raw material remains, then control the temperature below 5℃ and slowly pour the system into 200 ml of ice water, stir at 0-5℃ for 2 hours, 0-5℃ Stand at 5°C for 2 hours, filter, wash with a large amount of water until neutral, and dry under vacuum at 40°C for 24 hours to obtain 10.67 g of white or off-white solid, with a mass yield of 106.7%.

[0050] Preparation of ketal 4: Add 19.95 g of esterified product, 130 ml of ethylene glycol, and 90 ml of trimethyl orthoformate into the reaction flask in sequence under nitrogen protection, and stir at 20°C for 10 minutes, and the system becomes turbid. Finally, add 4 grams of p-toluenesulfonic acid, keep it warm at 20°C for an hour, then add 1 gra...

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Abstract

The invention relates to a preparation method of dehydroisoandrosterone. According to the preparation method, a compound 1 is prepared by a compound 2 through esterification reaction, ketalation reaction, reduction reaction and hydrolysis reaction. When the dehydroisoandrosterone is prepared by the chemical synthetic method, the defects of difficulty in control, cumbersome post treatment, high risk, pollution of the environment, and the like in traditional production method are avoided. Compared with the traditional production method, the reaction conditions of the preparation method are easyto control, the post treatment process is simple, and the yield is higher can be up to 80.79% after refining. Raw materials of the preparation method can be prepared by sterol through microbial fermentation, the raw materials are wide in sources, are cheap and relatively environmentally friendly and can be purchased from Hunan Nuokai Biological Pharmaceutical Co., Ltd, and the structural formulasof the compound 1 and the compound 2 are as follows.

Description

technical field [0001] The invention relates to a preparation method of dehydroepiandrosterone. Background technique [0002] DHEA is the main raw material for the manufacture of steroid hormones and contraceptives. The existing process uses diosgenin as a raw material to undergo reactions such as protection, oxidative cracking, elimination, oxime formation, Beckmann rearrangement, and hydrolysis. The steps are long, and the wastewater from the oxidation reaction is not easy to handle and easily pollutes the environment. [0003] The Chinese patent application number is 201110085711.X, and the patent literature with publication number 102212099A discloses a method for synthesizing dehydroepiandrosterone, which includes oximation of acetic acid pregnant dienolone, Beckmann rearrangement, hydrolysis, and refining to obtain The product is characterized in that the oximation of ketone uses sodium acetate as base, water and ethanol as solvent, Beckmann rearrangement, hydrolysis,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
Inventor 刘喜荣蒋青锋
Owner 湖南成大生物科技有限公司
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