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Synthetic method for medicinal hormone intermediate 11-keto-16alpha,17alpha-epoxyprogesterone

A technology of epoxy progesterone and a synthesis method, applied in the field of organic synthesis, can solve the problems that the reaction process does not conform to green environmental protection, the environmental pollution is large, and the physical cost is high, and the reaction time is shortened, the late pollution is reduced, and the reaction yield is improved. Effect

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

AI Technical Summary

Problems solved by technology

Most of the existing synthetic methods use chromium oxide, acetic acid and manganese chloride as reactants. Because chromium oxide and manganese chloride are relatively polluting to the environment, the reaction process does not meet the requirements of green environmental protection, and the physical cost of pollution control in the later stage is relatively high. The process technology is relatively complicated, so it is necessary to propose a new synthetic method

Method used

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  • Synthetic method for medicinal hormone intermediate 11-keto-16alpha,17alpha-epoxyprogesterone

Examples

Experimental program
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Effect test

Embodiment 1

[0017] The synthetic method of pharmaceutical hormone intermediate 11-keto-16α, 17α-epoxyprogesterone comprises the following steps:

[0018] A: Add 2mol 2-bromo-11α-hydroxyl-14-amino-16α, 17α-epoxy progesterone in reaction vessel, 1.8L mass fraction is 15% sodium sulfate solution, control stirring speed 150rpm, control solution temperature to 10°C, react for 50min;

[0019] B: Add 4 mol mass fraction of 20% ethyl furoate solution, 2 mol antimony trichloride powder, raise the solution temperature to 30°C, react for 1h, add 2L of 10% potassium chloride solution, let stand for 2h , precipitated crystals, filtered, washed twice with 20% sodium nitrate solution, 4 times with 50% 2,6-lutidine solution, 55% difluorodichloromethane The solution was washed 3 times, recrystallized in a solution of diethylene glycol methyl ethyl ether with a mass fraction of 80%, and dehydrated with anhydrous magnesium sulfate dehydrating agent to obtain 673.74 g of the finished product 11-keto-16α, 17...

Embodiment 2

[0021] The synthetic method of pharmaceutical hormone intermediate 11-keto-16α, 17α-epoxyprogesterone comprises the following steps:

[0022] A: Add 2mol 2-bromo-11α-hydroxyl-14-amino-16α, 17α-epoxy progesterone in reaction vessel, 1.8L mass fraction is 17% sodium sulfate solution, control stirring speed 160rpm, control solution temperature to 14°C, react for 60 minutes;

[0023] B: adding 5 mol mass fraction is 23% ethyl furoate solution, 2.5 mol antimony trichloride powder, raising the solution temperature to 34°C, reacting for 1.5h, adding 2L mass fraction is 15% potassium chloride solution, static Set aside for 2.5h, precipitate crystals, filter, wash 3 times with 24% sodium nitrate solution, 5 times with 55% 2,6-lutidine solution, 59% difluoro Dichloromethane solution was washed 4 times, recrystallized in 85% diethylene glycol methyl ethyl ether solution, and dehydrated with activated alumina dehydrating agent to obtain 1017.792g of finished product 11-keto-16α, 17α-epox...

Embodiment 3

[0025] The synthetic method of pharmaceutical hormone intermediate 11-keto-16α, 17α-epoxyprogesterone comprises the following steps:

[0026] A: Add 2mol 2-bromo-11α-hydroxyl-14-amino-16α, 17α-epoxy progesterone in reaction vessel, 1.8L mass fraction is 22% sodium sulfate solution, control stirring speed 170rpm, control solution temperature to 16°C, react for 70 minutes;

[0027] B: Add 6 mol mass fraction of 25% ethyl furoate solution, 3 mol antimony trichloride powder, raise the solution temperature to 35°C, react for 2h, add 2L of 17% potassium chloride solution, let stand for 3h , precipitated crystals, filtered, washed 4 times with 26% sodium nitrate solution, 6 times with 57% 2,6-lutidine solution, 62% difluorodichloromethane The solution was washed 5 times, recrystallized in a diethylene glycol methyl ethyl ether solution with a mass fraction of 86%, and dehydrated with anhydrous calcium chloride dehydrating agent to obtain 1021.896 g of finished product 11-keto-16α, 1...

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Abstract

Directed at technical problems in the prior art, the invention provides a synthetic method for the medicinal hormone intermediate 11-keto-16alpha,17alpha-epoxyprogesterone. The synthetic method comprises the following steps: adding 2-bromo-11alpha-hydroxy-14-amino-16alpha,17alpha-epoxyprogesterone and a sodium sulfate solution into a reaction vessel, controlling a stirring speed and a solution temperature, and carrying out a reaction; and adding an ethyl furoate solution and antimony trichloride powder, raising the solution temperature, carrying out a reaction, adding a potassium chloride solution, carrying out standing, allowing a crystal to be precipitated, carrying out filtering, washing the crystal with a sodium nitrate solution a plurality of times, then washing the crystal with a 2,6-lutidine solution a plurality of times, then washing the crystal with a methyl chlorofluoride solution a plurality of times, carrying out recrystallization in a diethylene glycol methyl ethyl ether solution and then carrying out dehydration with a dehydrating agent so as to obtain the finished 11-keto-16alpha,17alpha-epoxyprogesterone.

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 synthesis method of a pharmaceutical hormone intermediate 11-keto-16α, 17α-epoxy progesterone. Background technique [0002] 11-keto-16α, 17α-epoxyprogesterone is used as a medical hormone intermediate, mainly used in the synthesis of cortisone acetate, which is an intermediate of prednisone acetate. Itself is an anti-inflammatory agent. For the treatment of adrenal hypofunction, rheumatoid arthritis, rheumatism, lupus erythematosus and other diseases. Most of the existing synthetic methods use chromium oxide, acetic acid and manganese chloride as reactants. Because chromium oxide and manganese chloride are relatively polluting to the environment, the reaction process does not meet the requirements of green environmental protection, and the physical cost of pollution control in the later stage is relatively hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00
CPCC07J71/001
Inventor 关艮安
Owner CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING