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16-beta methylpregnene steroid hormone intermediate and preparation method of 16-beta methylpregnene steroid hormone intermediate

A technology of methylpregnene steroids and intermediates, which is applied in the field of 16-beta methylpregnene steroid hormone intermediates and their preparation, can solve the problems of long synthesis route and high cost of intermediates, and achieves reduction of three wastes "Effects of emissions, reduced consumption, shortened synthetic routes

Inactive Publication Date: 2017-05-24
CHINA UNIV OF PETROLEUM (EAST CHINA)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the intermediate synthesis route described in this route is longer and the cost is higher

Method used

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  • 16-beta methylpregnene steroid hormone intermediate and preparation method of 16-beta methylpregnene steroid hormone intermediate
  • 16-beta methylpregnene steroid hormone intermediate and preparation method of 16-beta methylpregnene steroid hormone intermediate
  • 16-beta methylpregnene steroid hormone intermediate and preparation method of 16-beta methylpregnene steroid hormone intermediate

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Experimental program
Comparison scheme
Effect test

Embodiment 1、16

[0071] The preparation of embodiment 1,16-beta methylpregnene steroid hormone intermediate compound (I)

[0072] (1) Ketal reaction:

[0073] Add 10 g of compound (II) to 100 g of tetrahydrofuran, add 0.01 g of concentrated sulfuric acid and 15 g of ethylene glycol, and stir the reaction at 20°C for 4 hours; concentrate under reduced pressure to remove the organic solvent, add methanol for recrystallization, and obtain compound (III);

[0074]

[0075] (2) Grignard reaction:

[0076] Add 10 g of compound (III) to 20 g of the Grignard reaction solution, heat to reflux for 25 hours, cool down to room temperature, pour the reaction solution into a saturated ammonium chloride solution, stir and analyze in water for 2 hours to obtain compound (IV);

[0077]

[0078] (3) Hydrolysis reaction

[0079] Add 10 g of compound (IV) to 20 g of glacial acetic acid, heat to reflux for 30 minutes, cool to room temperature, and pour the reactant into water to obtain compound (I).

[00...

Embodiment 2、16

[0082] The preparation of embodiment 2, 16-beta methylpregnene steroid hormone intermediate compound (I)

[0083] (1) Ketal reaction:

[0084] Add 10 g of compound (II) to 200 g of chloroform, add 0.01 g of p-tolueneboronic acid and 20 g of ethylene glycol, and stir and react at 50°C for 4 hours; concentrate under reduced pressure to remove the organic solvent, add ethanol for recrystallization, and obtain Compound (III);

[0085] (2) Grignard reaction:

[0086] Add 10 g of compound (III) to 15 g of Grignard reaction solution, heat to reflux for 25 hours, cool down to room temperature, pour the reaction solution into a saturated ammonium chloride solution, stir and analyze in water for 2 hours to obtain compound (IV);

[0087] (3) Hydrolysis reaction

[0088] Add 10 g of compound (IV) to 50 g of glacial acetic acid, heat to reflux for 30 minutes, cool to room temperature, and pour the reactant into water to obtain compound (I).

[0089] The overall yield of compound (I) wa...

Embodiment 3、16

[0090] The preparation of embodiment 3, 16-beta methylpregnene steroid hormone intermediate compound (I)

[0091] (1) Ketal reaction:

[0092] Add 10g of compound (II) to 30g of dichloromethane, add 0.01g of phosphorus trichloride and 20g of ethylene glycol, stir and react at 30°C for 4 hours; concentrate under reduced pressure to remove the organic solvent, dichloromethane, add propanol for re- crystallization to obtain compound (III);

[0093] (2) Grignard reaction:

[0094] Add 10 g of compound (III) to 30 g of the Grignard reaction solution, heat to reflux for 25 hours, cool down to room temperature, pour the reaction solution into a saturated ammonium chloride solution, stir and analyze in water for 2 hours to obtain compound (IV);

[0095] (3) Hydrolysis reaction

[0096] Add 10 g of compound (IV) to 30 g of glacial acetic acid, heat to reflux for 30 minutes, cool to room temperature, and pour the reactant into water to obtain compound (I).

[0097] The overall yield...

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Abstract

The invention relates to a 16-beta methylpregnene steroid hormone intermediate and a preparation method of the 16-beta methylpregnene steroid hormone intermediate. The intermediate has a structure shown as a formula (I). The intermediate is obtained by taking a mildew fermentation product as a raw material through three steps including ketal protection, Grignard reaction and hydrolysis reaction. The intermediate can be used for synthesizing a betamethasone steroid hormone crude drug, and the substance is used as the intermediate, so that a synthesis route of betamethasone can be greatly shortened, the cost is reduced and emission of three wastes is reduced. The formula (I) is shown as the description.

Description

technical field [0001] The invention relates to a 16-beta-methylpregnene steroid hormone intermediate and a preparation method thereof, belonging to the technical field of pharmacy. Background technique [0002] Betamethasone, chemical name: 16β-methyl-11β, 17α, 21-trihydroxy-9α-fluoro-pregna-1,4-diene-3,20-dione, molecular formula: C 22 h 29 FO 5 , which has a structure shown in formula (V), is a kind of hormone bulk drug with wide application. [0003] [0004] 16-β-methylpregnene intermediates are important intermediates for the preparation of steroidal APIs such as betamethasone. The existing methods for preparing betamethasone are: [0005] Using mold fermentation product: 11α-hydroxy-(16,17)-epoxy-4-enpregnene-3,20-dione as raw material, after Platts oxidation reaction, to obtain Platts oxide: (16,17) - epoxy-4-ene-pregna-3,11,20-trione; [0006] The Platinum oxide undergoes ketal reaction to obtain the ketal product 11 ketone-(16,17)-epoxy-4-enpregna-3,20-dike...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/0055
Inventor 李良军赵学波王颖代鹏程顾鑫
Owner CHINA UNIV OF PETROLEUM (EAST CHINA)
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