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Synthetic method for hormone drug intermediate 9(11)-pregnene-16beta-methyl-17alpha,21-diol-3,20-dione-21-acetate

A synthetic method, the technology of pregnene, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of unsuitability for large-scale industrial production, complex synthesis process, and increased risk, so as to shorten the reaction time, increase the reaction yield, The effect of avoiding pollution

Inactive Publication Date: 2018-07-03
CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Most of the existing synthetic methods use sodium dichromate solution and sulfuric acid solution as reactants. Because sodium dichromate solution pollutes the environment relatively large, it is not suitable for large-scale industrial production. Doing reactants with sulfuric acid solution will cause the risk of the reaction process to rise. high, and the whole synthesis process is relatively complicated, so it is necessary to propose a new synthesis method

Method used

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  • Synthetic method for hormone drug intermediate 9(11)-pregnene-16beta-methyl-17alpha,21-diol-3,20-dione-21-acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The synthetic method of hormone drug intermediate 9(11)-pregnene-16β-methyl-17α, 21-diol-3,20-diketone-21-acetate comprises the following steps:

[0018] A: Add 3mol 2-chloro-4-hydroxy-9(11)-pregnene-16β-methyl-3β,17α,21-triol-20-keto-21-acetate in the reaction vessel, 1.6L A potassium chloride solution with a mass fraction of 15%, a 2-picoline solution with a mass fraction of 30%, lower the temperature of the solution to 10° C., control the stirring speed at 210 rpm, and continue the reaction for 30 min;

[0019] B: Add 6 mol of diisobutylamine solution with a mass fraction of 40%, raise the solution temperature to 30°C, react for 50min, add 2mol of antimony hydrogen powder, raise the temperature to 40°C, react for 30min, let stand for 1h, filter, Obtain crystal, wash with the sodium nitrate solution that mass fraction is 10%, the benzonitrile solution that mass fraction is 40% washs, the p-bromochlorobenzene solution that mass fraction is 50% washs, the diethylene gly...

Embodiment 2

[0021] The synthetic method of hormone drug intermediate 9(11)-pregnene-16β-methyl-17α, 21-diol-3,20-diketone-21-acetate comprises the following steps:

[0022] A: Add 3mol 2-chloro-4-hydroxy-9(11)-pregnene-16β-methyl-3β,17α,21-triol-20-keto-21-acetate in the reaction vessel, 1.6L A potassium chloride solution with a mass fraction of 18%, a 2-picoline solution with a mass fraction of 33%, lower the temperature of the solution to 14° C., control the stirring speed at 220 rpm, and continue the reaction for 40 min;

[0023] B: Add 6.5mol of diisobutylamine solution with a mass fraction of 44%, raise the temperature of the solution to 33°C, react for 65min, add 2.5mol of antimony hydrogen powder, raise the temperature to 42°C, react for 35min, and let stand for 1.5h , filtered to obtain crystals, washed with 14% sodium nitrate solution with a mass fraction, washed with a 45% benzonitrile solution, washed with a 53% p-bromochlorobenzene solution, and washed with a 75% di Recrystal...

Embodiment 3

[0025] The synthetic method of hormone drug intermediate 9(11)-pregnene-16β-methyl-17α, 21-diol-3,20-diketone-21-acetate comprises the following steps:

[0026] A: Add 3mol 2-chloro-4-hydroxy-9(11)-pregnene-16β-methyl-3β,17α,21-triol-20-keto-21-acetate in the reaction vessel, 1.6L A potassium chloride solution with a mass fraction of 22%, a 2-picoline solution with a mass fraction of 36%, lower the temperature of the solution to 15° C., control the stirring speed at 230 rpm, and continue the reaction for 50 min;

[0027] B: Add 7 mol of diisobutylamine solution with a mass fraction of 45%, raise the solution temperature to 36°C, react for 80min, add 3mol of antimony hydrogen powder, raise the temperature to 45°C, react for 40min, let stand for 2h, filter, Obtain crystal, be that the sodium nitrate solution washing of 16% with mass fraction, the benzonitrile solution washing that mass fraction is 47%, the p-bromochlorobenzene solution washing that mass fraction is 56%, the diet...

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Abstract

The invention discloses a synthetic method for the hormone drug intermediate 9(11)-pregnene-16beta-methyl-17alpha,21-diol-3,20-dione-21-acetate. The synthetic method comprises the following steps: adding 2-chloro-4-hydroxy-9(11)-pregnene-16beta-methyl-3beta,17alpha,21-triol-20-one-21-acetate, a potassium chloride solution and a 2-methylpyridine solution into a reaction vessel, lowering solution temperature, controlling a stirring speed and continuing a reaction; and adding a diisobutylamine solution, raising a solution temperature, carrying out a reaction, adding antimony hydride powder, raising the temperature, carrying out a reaction, then carrying out standing and filtering successively so as to obtain a crystal, washing the crystal with a sodium nitrate solution, then washing the crystal with a benzonitrile solution, washing the crystal with a p-bromochlorobenzene solution, carrying out recrystallization in a diethylene glycol dibutyl ester solution, and then carrying out dehydration with a dehydrating agent so as to obtain the finished 9(11)-pregnene-16beta-methyl-17alpha,21-diol-3,20-dione-21-acetate.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, belonging to the field of organic synthesis, in particular to a hormone drug intermediate 9(11)-pregnene-16β-methyl-17α,21-diol-3,20-dione - Synthetic method of 21-acetate. Background technique [0002] 9(11)-pregnene-16β-methyl-17α, 21-diol-3,20-diketone-21-acetate is used as an intermediate of hormone drugs and is mainly used in the synthesis of betamethasone. Betamethasone is a hormone drug. Mainly used for anti-inflammatory and anti-allergic. It is suitable for rheumatoid arthritis and various skin diseases. The effect of betamethasone is the same as that of dexamethasone, and its anti-inflammatory effect is stronger than that of dexamethasone, triamcinolone, and hydrocortisone, and has fewer side effects. Most of the existing synthetic methods use sodium dichromate solution and sulfuric acid solution as reactants. Because sodium dichromate solution pollutes the env...

Claims

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Application Information

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IPC IPC(8): C07J5/00
CPCC07J5/0076
Inventor 关艮安
Owner CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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