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A kind of fluoroalkylation method of steroid 17β-thiocarboxylic acid

A thiocarboxylic acid, fluoroalkylation technology, applied in the production of steroids, organic chemistry, bulk chemicals, etc., can solve the problems of high content, ineffective control of reaction conditions, and complicated post-processing procedures

Active Publication Date: 2022-08-09
TIANJIN PHARMA GROUP CORP
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the compound of formula I containing mercapto is easily oxidized, disulfide compound (-S-S-), mercapto oxide (-SOH), haloalkylated impurity (SOCH) introduced by mercapto oxidation 2 X), the existing reaction conditions cannot be effectively controlled, the content of fluoroformation products obtained is low, the content of impurity disulfide compounds and mercapto oxides is high, and it needs to be washed or crystallized many times, and the post-treatment procedure is complicated

Method used

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  • A kind of fluoroalkylation method of steroid 17β-thiocarboxylic acid
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  • A kind of fluoroalkylation method of steroid 17β-thiocarboxylic acid

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Experimental program
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Effect test

Embodiment 1

[0063]

[0064] 50ml of dimethylacetamide and 10g of compound 1 were added to a four-neck reaction flask, cooled to -5°C, 2.9g of sodium sulfite was added, 2.0ml of bromofluoromethane was added dropwise, 500ml of purified water was added after the reaction was complete, a solid was precipitated, and the Filtration to obtain 10.4 g of compound 2 crude product, the detected compound 2 content is 98.8%, the mercapto oxide content is 0.38%, the haloalkylated impurity is 0.19%, and the disulfide compound is not detected. The obtained solid compound 2 crude product is added to absolute ethanol for recrystallization , suction filtration, and drying to obtain 10.1 g of compound 2, the content of which is 99.7%.

Embodiment 2

[0068]

Embodiment 2-1

[0070] Add 100ml of acetonitrile and 10g of compound 3 into a four-neck reaction flask, cool down to -15°C, add 4.0g of potassium carbonate and 1.0g of potassium sulfite, then dropwise add 2.0ml of fluoroiodomethane, add 500ml of purified water after complete reaction, and precipitate out Solid, suction filtration to obtain 10.3 g of compound 4 crude product, content 98.8%, mercapto oxide content 0.40%, haloalkylated impurities 0.21%, no disulfide compounds detected. The obtained solid compound 4 crude product was added to absolute ethanol for recrystallization, suction filtration, and dried to obtain 9.8 g of compound 4 fine product, with a content of 99.2%.

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Abstract

The invention provides a fluoroalkylation method of steroid 17β-thiocarboxylic acid: a compound of formula I, which reacts with F-CH under the condition that a reducing salt is used as a catalyst 2 -X reagent reacts to obtain the fluoroalkylated compound of formula II of 17β-thiocarboxylic acid, where X is halogen. The invention uses a reducing inorganic salt as a catalyst, which greatly reduces the generation of disulfide impurities, mercapto oxide impurities, and halogenated alkylate impurities introduced by mercapto oxides.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a fluoroalkylation method of steroid 17β-thiocarboxylic acid. Background technique [0002] Carbon-fluorine bonds are commonly found in pharmaceutical products, such as fluticasone propionate, fluticasone furoate, fluoroquinone, etc. Fluoroalkylation is one of the main synthetic methods for the preparation of fluorinated organic compounds. The reaction is generally based on compounds with a sulfhydryl (-SH) structure and bromofluoromethane (fluorochloromethane, fluoroiodomethane) under the catalysis of organic amines or inorganic carbonates. The reaction introduces a fluoromethyl group. Since the thiol-containing compound of formula I is easily oxidized, disulfide compounds (-S-S-), thiol oxides (-SOH), halogenated impurities (SOCH) introduced by thiol oxidation are generated. 2 X), the existing reaction conditions cannot be effectively controlled, the content of the obtained ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J31/00C07J71/00
CPCC07J31/006C07J71/0015C07J71/0031C07J71/0068Y02P20/55
Inventor 李亚玲张亮
Owner TIANJIN PHARMA GROUP CORP
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