Method for synthesizing desonide impurity

A synthesis method and technology of mixed solution, applied in steroids, organic chemistry and other directions, can solve problems such as complicated operation, and achieve the effects of simple operation, favorable for industrial production and mild method conditions

Pending Publication Date: 2021-06-01
CHONGQING HUABANGSHENGKAI PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The synthesis of 11β,16α,17α-trihydroxypregna-1,4-diene-3,20-dione-21-aldehyde-16,17-acetal acetone has no relevant literature, only similar reactions have been reported J. Org.Chem.2002, 67, 6835-6836, is to use copper sulfate to catalyze the oxidation, and then prepare the product through magnesium silicate (Florisil) solid-phase extraction column. This method requires special equipment and complicated operation

Method used

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  • Method for synthesizing desonide impurity
  • Method for synthesizing desonide impurity
  • Method for synthesizing desonide impurity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Add 2g of desonide and 0.5g of copper acetate into a 250ml three-neck flask, fully dissolve in 150ml of methanol to form a solution, when the solution is heated to 30°C, blow air into the solution to react to obtain a reaction solution, the reaction solution is pale yellow, and the reaction After 2h, TLC (CH2Cl2:CH3OH 15:1) test showed that the reaction of the raw materials was complete, and the reaction was stopped; 150ml of water was added to the reaction solution, and the aqueous layer was extracted twice with 250ml of dichloromethane respectively, and the organic layers extracted twice were combined and washed with water. The organic layer was concentrated under reduced pressure to dryness to obtain a white solid.

[0038] Add 250ml of acetonitrile to the white solid, stir to dissolve, add 80ml of water and 2 drops of phosphoric acid, react at 40-50°C for 1 hour, the product monitored by HPLC is 96%, stop the reaction; evaporate the acetonitrile under reduced pressur...

Embodiment 2

[0045] Add 2g of desonide and 0.2g of copper acetate to a 250ml three-neck flask, fully dissolve in 150ml of methanol to form a solution, and when the solution is heated to 30°C, blow air into the solution to react to obtain a reaction solution. After 2h, TLC (CH2Cl2:CH3OH 15:1) test showed that the reaction of the raw materials was complete, and the reaction was stopped; 150ml of water was added to the reaction solution, and the aqueous layer was extracted twice with 250ml of dichloromethane respectively, and the organic layers extracted twice were combined and washed with water. The organic layer was concentrated under reduced pressure to dryness to obtain a white solid.

[0046] Add 150ml of acetone to the white solid, stir to dissolve, add 80ml of water and 2 drops of phosphoric acid, react at 40-50°C for 1 hour, the product monitored by HPLC is 94%, and the reaction is stopped; the acetone is evaporated under reduced pressure, and 250ml of dichloro Extracted twice with me...

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Abstract

The invention discloses a method for synthesizing desonide impurity 11 [beta], 16 [alpha], 17 [alpha]-trihydroxypregna-1, 4-diene-3, 20-dione-21 aldehyde-16, 17-acetal acetone. The method comprises the following steps: taking desonide as an initial raw material, catalyzing by using anhydrous cupric sulfate, introducing air to oxidize, carrying out hydrolysis reaction under the catalysis of acid, and drying by using sodium sulfate to obtain the desonide impurity 11 [beta], 16 [alpha], 17 [alpha]-trihydroxypregna-1, 4-diene-3, 20-dione-21 aldehyde-16, 17-acetal acetone. The synthesis route is short, the reaction condition is mild, the impurity can be obtained without column chromatography, and the purity of the obtained impurity is 97% or above.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a method for synthesizing desonide impurities. Background technique [0002] Desonide is a glucocorticoid drug, which has anti-inflammatory, anti-allergic, anti-itching and reducing exudation effects; it can reduce and prevent tissue responses to inflammation, and can eliminate fever, redness and swelling caused by local non-infectious inflammation , thereby reducing the manifestations of inflammation; it has the immunosuppressive effect of preventing or inhibiting cellular immune response and suppressing the primary immune response. [0003] The chemical name of desonide is 11β,16α-17,21-tetrahydroxypregna-1,4-diene-3,20-dione ring 16,17-acetal acetone, and its structural formula is as follows: Formula I: [0004] [0005] There are many impurities in desonide, one of which is 11β,16α,17α-trihydroxypregna-1,4-diene-3,20-dione-21 aldehyde-16,17-acetal acetal,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00
CPCC07J71/0031
Inventor 朱强
Owner CHONGQING HUABANGSHENGKAI PHARM
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