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High-purity ethinyloestradiol synthesis method

A synthesis method and technology of ethinyl estradiol are applied in the field of synthesis of estrogen ethinyl estradiol, which can solve the problem that the ratio of epimers in the ethynylation product cannot be effectively controlled, and the industrial production of ethinyl estradiol cannot be satisfied, and the yield and The problem of low content, etc., to achieve the effect of easy control of generation conditions, significant comprehensive economic benefits, and high content

Inactive Publication Date: 2013-07-17
湖北三晶生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] But all there is major defect in above-mentioned four kinds of production techniques: promptly the reagent price used in the production technique is expensive, and reaction time is too long, and acetylene consumption is big, can't effectively control the ratio of epimer in the alkynylation product, and yield The rate and content are not high enough to meet the needs of industrial production of ethinyl estradiol
[0014] According to the search, there is no patent application identical to the present invention in China

Method used

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Examples

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Embodiment 1

[0035] The preparation of the first step potassium alkyne:

[0036] Add 20g of potassium hydroxide powder with a water content of 13% into a three-necked reaction bottle, pass in acetylene gas to replace the air in the bottle, then seal it, then pass in normal pressure acetylene gas from the metering bottle, start stirring and heat up in a water bath, about 40°C When the inspiratory volume reaches 2.2L and the temperature reaches 75°C, the heating is stopped and cooled to room temperature under stirring to obtain the crude product of light brown powdery potassium alkyne and potassium hydroxide mixture with a potassium alkyne content of 10 %, sealed and kept for later use;

[0037] The preparation of second step ethinyl estradiol:

[0038] Add 45g of potassium alkyne powdered crude product and 45ml of THF to the three-necked reaction flask, blow out the air in the bottle with acetylene gas while stirring, keep the reaction temperature at -5~5°C, and add 5g of estrone and 0.15m...

Embodiment 2

[0040] The preparation of the first step potassium alkyne:

[0041] Add 100g of potassium hydroxide powder with a water content of 6% into a three-necked reaction bottle, pass in acetylene gas to replace the air in the bottle, then seal it, then pass in normal pressure acetylene gas from the metering bottle, start stirring and heat up in a water bath, about 40°C When the inspiratory volume reaches 12L and the temperature reaches 80°C, the heating is stopped and cooled to room temperature under stirring to obtain the crude product of light brown powdery potassium alkyne and potassium hydroxide mixture with a potassium alkyne content of 12%. , sealed and kept for later use;

[0042] The preparation of second step ethinyl estradiol:

[0043] Add 80g of potassium alkyne powdered crude product and 110ml of THF to the three-necked reaction flask, blow out the air in the bottle with acetylene gas while stirring, keep the reaction temperature at 0~10°C, add 10g of estrone and 0.15ml ...

Embodiment 3

[0045] The preparation of the first step potassium alkyne:

[0046] Put 250g of potassium hydroxide powder with a water content of 12% into a three-necked reaction bottle, pass in acetylene gas to replace the air in the bottle, then seal it, then pass in normal pressure acetylene gas from the metering bottle, start stirring and heat up in a water bath, at about 40°C Start to absorb acetylene, when the inspiratory volume reaches 24L and the temperature reaches 85°C, stop heating and cool to room temperature under stirring to obtain the crude product of light brown powdery mixture of potassium alkyne and potassium hydroxide, the content of potassium alkyne is 11%. Sealed and kept for later use;

[0047] The preparation of second step ethinyl estradiol:

[0048] Add 200g of potassium alkyne powdered crude product and 170ml of THF to the three-necked reaction flask, blow out the air in the bottle with acetylene gas while stirring, keep the reaction temperature at 0~10°C, and add ...

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Abstract

A high-purity ethinyloestradiol synthesis method relates to a synthesis method of estrogen ethinyloestradiol, and in particular relates to a synthesis method for synthesizing high-purity ethinyloestradiol by using estrone and acetylene potassium. The synthesis method comprises two steps as follows:1, reacting potassium hydroxide powder with an acetylene gas to obtain acetylene potassium; and 2, reacting the estrone with the acetylene potassium so as to obtain the ethinyloestradiol at a high content. The high-purity ethinyloestradiol synthesis method has a simple technical condition, no need of expensive reagents, low production cost, easily controlled industrial generation condition, fast reaction speed, high production efficiency, high yield, high content and good product quality, meets the standard of European pharmacopoeia, achieves obvious comprehensive economic benefits, solves the problems that reagents used in the conventional production technology are expensive, the reaction time is long, the consumption amount of acetylene, is great, the proportion of epimers in an ethynylation product cannot be controlled efficiently, the yield and content are low, and the demands on industrial production of the ethinyloestradiol cannot be satisfied, and can be popularized and applied to all the ethinyloestradiol production enterprises.

Description

technical field [0001] The invention relates to a method for synthesizing estrogen ethinyl estradiol, in particular to a method for synthesizing high-purity ethinyl estradiol by reacting estrone and ethinyl potassium. Background technique [0002] Ethinyl estradiol is an estrogen, its chemical name is 3-hydroxy-19-nor-17α-pregna-1,3,5(10)-triene-20-yn-17-ol, the English name is Ethinyl estradiol. The combination of ethinyl estradiol and drospirenone constitutes Yasmin contraceptive, which is currently a low-dose oral contraceptive with good safety, efficacy and tolerability. [0003] There are four methods for the production of ethinyl estradiol at present: the introduction of ethynyl groups by adding some metal acetylides to hydroxyl groups. The metal acetylides are prepared from Grignard reagents or from metals such as sodium, potassium, lithium and potassium isobutoxide. Below are the chemical structural formulas of the production routes of metal alkylides by four meth...

Claims

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Application Information

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IPC IPC(8): C07J1/00
Inventor 尹宏任学成程杏芳
Owner 湖北三晶生物科技股份有限公司
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