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Production method of 16-dehydropregnenolone acetate oxime

A technology of acetic acid pregnant dienolone and dienolketoxime, which is applied in the field of production technology of steroid hormone drug intermediates, and achieves the effects of high product quality, simple operation and good reaction selectivity

Inactive Publication Date: 2014-11-19
TIANJIN FOREVER GREEN BIOLOGICAL PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to overcome the defects of the oximation reaction in the above literature. The new method of the present invention uses a mixed solvent to solve the solubility of dienolone acetate and hydroxylamine hydrochloride. The rate of the chemical reaction and the effect of the water formed in the reaction on the reaction

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  • Production method of 16-dehydropregnenolone acetate oxime
  • Production method of 16-dehydropregnenolone acetate oxime
  • Production method of 16-dehydropregnenolone acetate oxime

Examples

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specific Embodiment 1

[0042] Embodiments of the invention:

[0043]In 50 liters of reactors, add 7 kilograms of acetic acid pregnant dienolones, 3.5 kilograms of pyridine, 25 kilograms of solvent methanol, 8 kilograms of solvent dichloroethanes, add 1.6 kilograms of hydroxylamine hydrochloride, 0.007 kilograms of N, N from the solid feeding port - lutidine, stirring and heating until the temperature of the reaction kettle reaches reflux, keeping the reflux reaction for 1 hour and 30 minutes, sampling and detecting the content of acetic acid pregnant dienolone. Stop heating until the content of dienolone in acetic acid pregnancy is below 0.5%, pass through cooling water to cool to about 10°C, stir at about 10°C for 30 minutes, filter, and rinse the filter cake with 2-5 kg ​​of reaction mixed solvent Twice, the filter cake was dried to obtain 7 kilograms, and the liquid chromatography standard sample method detection content was 99%. The molar yield was 95.8%. The filtrate was dried and weighed wit...

specific Embodiment 2

[0065] In 50 liters of reactors, add 7 kilograms of acetic acid pregnant dienolones, 3.5 kilograms of pyridine, 25 kilograms of solvent ethanol, 8 kilograms of solvent dichloroethanes, add 1.6 kilograms of hydroxylamine hydrochloride, 0.007 kilograms of N, N from the solid feeding port - lutidine, stirring and heating until the temperature of the reaction kettle reaches reflux, keeping the reflux reaction for 1 hour and 30 minutes, sampling and detecting the content of acetic acid pregnant dienolone. Stop heating until the content of dienolone in acetic acid pregnancy is below 0.5%, pass through cooling water to cool to about 10°C, stir at about 10°C for 30 minutes, filter, and rinse the filter cake with 2-5 kg ​​of reaction mixed solvent Twice, the filter cake was dried to obtain 7 kilograms, and the liquid chromatography standard sample method detection content was 98%. The molar yield was 94.1%. The filtrate was dried and weighed with anhydrous sodium sulfate, and the rati...

specific Embodiment 3

[0076] In 50 liters of reactors, add 7 kilograms of acetic acid pregnant dienolones, 3.5 kilograms of pyridine, 25 kilograms of solvent ethanol, 5 kilograms of solvent chloroforms, add 1.6 kilograms of hydroxylamine hydrochloride, 0.007 kilograms of N, N- lutidine, stirring and heating until the temperature of the reaction kettle reaches reflux, keeping the reflux reaction for 1 hour and 30 minutes, sampling and detecting the content of acetic acid pregnant dienolone. Stop heating until the content of dienolone in acetic acid pregnancy is below 0.5%, pass through cooling water to cool to about 10°C, stir at about 10°C for 30 minutes, filter, and rinse the filter cake with 2-5 kg ​​of reaction mixed solvent Twice, the filter cake was dried to obtain 7.1 kg, and the detection content by the liquid chromatography standard sample method was 98.5%. The molar yield was 95.9%. The filtrate was dried and weighed with anhydrous sodium sulfate, and the ratio of ethanol and chloroform w...

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Abstract

The invention provides a novel production method of 16-dehydropregnenolone acetate oxime. The novel production method comprises the following steps: on the basis of taking 16-dehydropregnenolone acetate as a raw material, alcohol or halohydrocarbon or arene as a solvent and organic base or inorganic base as an acid-binding agent, reacting by using hydroxylammonium chloride, then crystallizing and drying to obtain 16-dehydropregnenolone acetate oxime. The novel production method has the remarkable characteristics that the dissolving property problem of 16-dehydropregnenolone acetate and hydroxylammonium chloride is solved by using the mixed solvent, and meanwhile, a water absorbent and a catalyst are added, so that the influences of oximation reaction speed and the generated water on the reaction are eliminated. Compared with the traditional method, the novel production method provided by the invention has the remarkable advantages that the reaction speed is high, and the reaction time is at least shortened to less than 1 / 2 of the time needed by using the traditional method; the reaction selectivity is good, the yield is high, and the molar yield is up to 99% which is five times as high as that of the traditional method; the quality of 16-dehydropregnenolone acetate oxime is high, and the content of 16-dehydropregnenolone acetate oxime is up to more than 98%; the process is clean, and less wastewater is generated; and the novel production method is simple and convenient to operate and can be used for easily realizing industrial production.

Description

Technical field: [0001] The invention relates to a production process of a steroid hormone drug intermediate, in particular to a production method of acetic acid gestational dienol ketone oxime. Background technique: [0002] Pregnant dienol ketoxime acetate is an important raw material for the production of DHEA, and DHEA is an extremely important intermediate for the production of steroid hormone drugs. It is a synthetic testosterone, methyl testosterone, estradiol, estriol, stanozolol, norethindrone, mifepristone and other steroidal androgen, anabolic hormone, estrogen and progesterone and other hormone drugs important raw materials. At present, most enterprises in our country are using the traditional process described in the book "Compendium of Drug Synthesis Methods" published in the 1980s, that is, using acetic acid pregnant dienolone as raw material, using ethanol as solvent, and using hydroxylamine hydrochloride for synthesis. The oximation reaction, cooling and c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
Inventor 邹小毛刘殿甲许保友
Owner TIANJIN FOREVER GREEN BIOLOGICAL PHARMA TECH
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