Synthetic method of spironolactone

A synthesis method and spironolactone technology, applied in the field of chemical synthesis, can solve problems such as irritating odor of thioacetic acid, unfavorable sustainable development, high environmental protection pressure, etc., and achieve the effects of good economic value, beneficial to sustainable development, and easy operation.

Active Publication Date: 2012-01-18
ZHEJIANG LANGHUA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The thioacetic acid used in this process has a pungent smell and serious pollution, which lead

Method used

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  • Synthetic method of spironolactone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 12.25 g canrenone, 9.5 g oxalic acid, 6.2 g potassium thioacetate and 100 ml ethanol were added to the reaction vessel. Heat to reflux reaction for 3 hours, add 2.4g potassium thioacetate, and continue reflux reaction for 2 hours. After the reaction is completed, stop heating, cool down to -10°C, keep warm for 2 hours, filter, and filter cake with 10ml water and Rinse with 10ml of ethanol, dry to obtain 13.8g of crude product, and recrystallize with ethanol to obtain 12.25g, the total yield is 75%, HPLC99.2%.

Embodiment 2

[0024] Add 12.25g canrenone, 8.6g potassium thioacetate and 100ml ethanol into the reaction vessel, heat to reflux, slowly add 9.5g oxalic acid dropwise for 1 hour, and continue to react for 3 hours after the addition. After the reaction, stop heating, cool down to -10°C, keep warm for 1.8 hours, filter, filter cake with 10ml of water and 10ml of ethanol, and dry to obtain 13.5g of crude product, then recrystallize with ethanol to obtain 12.36g, The total yield is 75.8%, and the HPLC purity is 99.3%.

Embodiment 3

[0026] 12.25 g of canrenone, 8.6 g of potassium thioacetate and 100 ml of ethanol were added to the reaction vessel. Heat to reflux, slowly add 7.3g methanesulfonic acid dropwise for about 1 hour, and continue to react for 3 hours after the addition is complete. After the reaction is complete, stop heating, cool down to -10°C, keep warm for 2.2 hours, filter, filter the cake with 10ml of water and 10ml of ethanol, and dry to obtain 14.5g of crude product, which is then recrystallized with ethanol to obtain 12.43g , The total yield is 76%, and the HPLC purity is 99.0%.

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Abstract

A synthetic method of spironolactone belongs to the technical field of chemical synthesis. The method comprises the following steps: heating and refluxing for 3-5 hours to perform an addition reaction with canrenone and potassium thioacetate as raw materials and ethanol as a solvent in the presence of an acidic catalyst, after the reaction, cooling to -10 DEG C, performing heat preservation for 1.5-2.5 hours, filtering, treating the filter cake to obtain spironolactone, wherein the feeding molar ratio of canrenone, potassium thioacetate, and the acidic catalyst is 1:2.1:2.1. The invention adopts thiacetate instead of thioacetic acid, which effectively solves the environmental protection pressure caused by thioacetic acid, and reduces environment pollution; the method has a simple process, is easy to operate, and has high economic and environmental protection benefit; the invention mainly solves the technical problem of existing synthetic methods that the special smell of the raw material of thioacetic acid causes high environmental protection pressure for enterprises.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of spironolactone with simple process and good economic value. Background technique [0002] The chemical name of spironolactone (spironolactone I) is: (7α,17α)-7-(acetylthio)-17-hydroxy-3-oxopregna-4-ene-21-carboxylic acid-γ-lactone, which is derived from The mineralocorticoid antagonist developed by Pfizer of the United States is now on the market in many countries and is clinically used as a diuretic. The structure of spironolactone is as follows: [0003] [0004] The current literature reports that the preparation method of spironolactone is mainly prepared by reacting canrenone and thioacetic acid. The thioacetic acid used in this process has a pungent smell and serious pollution, which leads to great pressure on environmental protection and is not conducive to sustainable development. Contents of the invention [0005] ...

Claims

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Application Information

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IPC IPC(8): C07J21/00
Inventor 林邦平李军敏王小平
Owner ZHEJIANG LANGHUA PHARMA
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