Method for preparing spirolactone by chemical-enzymatic method

A technology for enzymatic preparation of spironolactone, applied in chemical instruments and methods, organic chemistry, lactone steroids, etc., can solve the problems of expensive reagents, pollution, unfriendly environment, etc., achieve good economic benefits, high commercial competitiveness, and avoid Effects of Security Risks

Active Publication Date: 2021-10-22
ZHEJIANG SHENZHOU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method has harsh reaction conditions, high requirements on equipment, difficult operation, many steps, expensive reagents, low total yield and high cost
[0005] The second is to use androstenedione as the starting material, and obtain the lactone compound through etherification, epoxidation, and lactonization, and then through bromination, dehydrobromination, and then addition reaction to obtain; the synthesis The method uses a bromi...

Method used

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  • Method for preparing spirolactone by chemical-enzymatic method
  • Method for preparing spirolactone by chemical-enzymatic method
  • Method for preparing spirolactone by chemical-enzymatic method

Examples

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example 1

[0041] Example 1 The preparation of 3-ethoxy-androst-3,5-dien-17-one

[0042] Put 30g of 4-androstene-3,17dione (4AD) into 15ml of absolute ethanol, add 18ml of triethyl orthoformate, 0.3g of p-toluenesulfonic acid, and keep warm at 40°C for reaction. After the reaction is completed, filter, Dry it to obtain 31.5 g of 3-ethoxy-androst-3,5-dien-17-one.

example 2

[0043]Example 2 Preparation 2 of 3-ethoxy-androst-3,5-dien-17-one

[0044] Put 30g of 4-androstene-3,17dione (4AD) into 150ml of absolute ethanol, add 60ml of triethyl orthoformate, 0.15g of p-toluenesulfonic acid, keep warm at 42°C, and filter after the reaction is completed. Dry it to obtain 31.3 g of 3-ethoxy-androst-3,5-dien-17-one.

example 3

[0045] Example 3 Preparation of 3-ethoxy-androst-3,5-dien-17-one

[0046] Put 30g of 4-androstene-3,17dione (4AD) into 300ml of absolute ethanol, add 90ml of triethyl orthoformate, 0.3g of p-toluenesulfonic acid, keep warm at 45°C for reaction, after the reaction is completed, filter, Dry it to obtain 31.2 g of 3-ethoxy-androst-3,5-dien-17-one.

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Abstract

The invention discloses a method for preparing spirolactone by a chemical-enzyme method, and belongs to the technical field of organic synthesis. According to the method for preparing the spirolactone through the chemical-enzymatic method, 4AD serves as a raw material, and the spirolactone is obtained through enol etherification, epoxidation, lactonization, enzymatic dehydrogenation and sulfo-reaction. The enzymatic dehydrogenation method adopted by the spirolactone synthesis process route is good in specificity, mild in condition, free of special equipment and high in catalytic rate; the reaction product in each step involved in the method is easy to purify, the total mass yield of the final product is higher than 92%, and the HPLC purity is higher than 99.8%; the method is low in cost and suitable for industrial large-scale production, and has good economic benefits.

Description

【Technical field】 [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing spironolactone, in particular to a method for preparing spironolactone by combining chemical and enzymatic methods. 【Background technique】 [0002] Spironolactone is a weak potassium-sparing diuretic, also known as spironolactone and spironolactone. It is a white or off-white fine crystalline powder with a slight bitter taste, odorless or a slight thiol odor. Easily soluble in chloroform, insoluble in water, soluble in ethanol, soluble in benzene or ethyl acetate. The chemical structure is similar to that of aldosterone, which can compete with aldosterone for the aldosterone receptor in the cytoplasm of the distal convoluted tubule and collecting duct, affecting the binding of aldosterone to the receptor, thus hindering the synthesis of aldosterone-induced protein, thereby inhibiting the K+-Na+ exchange and reducing the excretion of potassium ,...

Claims

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Application Information

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IPC IPC(8): C12P33/20C07J21/00
CPCC12P33/20C07J21/003
Inventor 王友富邵振平王荣罗敏王洪福黄橙橙雷灵芝
Owner ZHEJIANG SHENZHOU PHARMA
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