Synthesis method of ethisterone

A synthesis method and a technology for ethinylprogesterone, which are applied in the field of pharmaceutical preparation, can solve the problems of low degree of reaction specificity, high proportion of side reactions, shortage of raw material resources and the like, and achieve the effects of low cost, short reaction route and wide supply of raw materials

Active Publication Date: 2015-12-16
ZHEJIANG XIANJU JUNYE PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The present invention proposes a new method for synthesizing progesterone in order to solve the shortcomings of the prior art such as shortage of raw material resources, long reaction steps, low degree of reaction specificity, high proportion of side reactions, high cost, and high energy consumption.

Method used

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  • Synthesis method of ethisterone
  • Synthesis method of ethisterone
  • Synthesis method of ethisterone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add 10 grams of 4AD, 40 milliliters of ethanol, 20 milliliters of dichloromethane, and 0.02 grams of PTS into the reaction bottle, stir, cool down to 10°C, add 9 milliliters of triethyl orthoformate, control the temperature at 18-20°C and keep the reaction for 120 minutes. Spot the plate (developer: petroleum ether: acetone = 5:2) the raw material spots basically disappear, add 50 ml of ice water to terminate the reaction, stir for 30-40 minutes, add triethylamine dropwise to adjust the pH to 8, and reduce the pressure below 50 °C Concentrate until the remaining amount of ethanol is 1W, then add 50 ml of water to cool down to about 20°C, stir for 2 hours, filter, and drain. Dry at 40°C. Control moisture at 0.2%. Yield: 110%.

[0037] Put 130 grams of toluene isobutanol, 55 grams of isobutanol, and 10 grams of potassium hydroxide into the reaction flask, stir and heat to reflux, control the distillation speed and atmospheric pressure distillation dehydration for 6 hour...

Embodiment 2

[0042] Add 10 grams of 4AD, 60 milliliters of methanol, 20 milliliters of dichloromethane, and 0.02 grams of PTS into the reaction flask, stir, cool down to 20°C, add 10 milliliters of triethyl orthoformate, control the temperature at 35°C for 180 minutes, and spot the plate (Developer: Petroleum ether: Acetone = 5:2) The raw material point basically disappears, add 50 ml of ice water to stop the reaction, stir for 30-40 minutes, add triethylamine dropwise to adjust pH = 8, and concentrate under reduced pressure below 50°C to The remaining amount of methanol is 2W, add 50 ml of water to cool down to about 25°C, stir for 2 hours, filter, and drain. Dry at 60°C. Control moisture at 0.2%. Yield: 110%.

[0043] Put 150 grams of toluene isobutanol, 65 grams of isobutanol, and 10 grams of potassium hydroxide into the reaction flask, stir and heat to reflux, control the distillation speed and atmospheric pressure distillation dehydration for 6 hours, and steam half of the toluene i...

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Abstract

The invention discloses a synthesis method of ethisterone which is prepared by adopting 4AD namely soybean oil tailings as a raw material, carrying out etherification protection as well as two-step reaction, namely, ethynylation and hydrolysis, and then refining. According to the invention, the raw material is replaced, that is the industrial tailing fermentation product 4AD of the soybean oil is used to replace diene; the raw material is wide in supply, low in cost and little in pollution; the reaction route is short; the process is simple; the auxiliary materials are commonly used chemical products; the generation amount of waste gas, waste water and waste solid is small and is a quarter of that generated in the traditional process.

Description

technical field [0001] The invention belongs to the field of medicine preparation, and relates to a method for synthesizing progesterone. Background technique [0002] The traditional production route of progesterone is to use diene as raw material, and it is prepared through 5 steps of chemical reactions including ketoxime, rearrangement, hydrolysis, acetylenylation and oxidation. The production route is long, the supply of raw materials is exhausted, the yield of the synthesis reaction is low, and highly toxic substances such as phosphorus oxychloride are used, resulting in a large amount of three wastes. The overall cost of producing gestinyl is therefore high. [0003] The synthetic route is shown in formula 1: [0004] [0005] At the same time, with the rise of research on sterol resources, there are also studies using 4AD as a starting material to synthesize progesterone through a one-step ethynylation reaction. Compared with the traditional route, this route re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
Inventor 张峥斌胡明辉魏真董安邦
Owner ZHEJIANG XIANJU JUNYE PHARM CO LTD
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