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Preparation method of 17 alpha-hydroxyl steroid ester

A technology of hydroxy steroid ester and hydroxy steroid is applied in the field of preparation of 17α-hydroxy steroid ester and achieves the effects of being beneficial to environmental protection, simple process and mild reaction conditions

Active Publication Date: 2014-03-26
CHENGDU YILUKANG MEDICAL TECH & SERVICE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Michael J.Green, et al. use trifluoroacetic anhydride to carry out esterification (J.Med.Chem., 25,1492-1495,1982), the trifluoroacetic anhydride used in this method has volatility, irritation, in There are limitations in industrial production

Method used

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  • Preparation method of 17 alpha-hydroxyl steroid ester
  • Preparation method of 17 alpha-hydroxyl steroid ester
  • Preparation method of 17 alpha-hydroxyl steroid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-pregna-1,4-diene-3,20-dione 50g (127.4mmol), ethyl acetate 300ml, triethyl orthopropionate Put 50 g (283.7 mmol) of the ester and 1 g of p-toluenesulfonic acid into a reaction bottle, and stir and react at 50° C. for 2.5 hours. After the reaction was completed, ethyl acetate was recovered under reduced pressure. Then add 500ml of ethanol, 8g of L-glutamic acid, 300ml of water, stir and react at 50°C for 2 hours, filter out the insoluble matter (the insoluble matter is L-glutamic acid, which can be recycled and applied), wash the filter cake with an appropriate amount of ethanol, and combine Filtrate, ethanol recovery under reduced pressure. The residue was filtered and dried to obtain 9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-pregna-1,4-diene-3,20-dione-17-propionate white powder 53.7 g, yield 94.0%.

[0039] Melting point: 230-235°C

[0040] 1 H-NMR (CDCl 3 , 400MHZ): 1.06, 1.14, 1.16, 1.30, 1.36, 1.38, 1.41, 1.55, 1.63...

Embodiment 2

[0042] According to the method of Example 1, replace 11β, 17α, 21-trihydroxypregna-4-ene-3,20-dione with 11β, 17α, 21-trihydroxypregna-4-ene-3,20-dione , reacted with triethyl orthoacetate to obtain 53.8 g of 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione-17-acetate white powder, with a yield of 96.4%.

[0043] Melting point: 162-166°C

[0044] 1 H-NMR (CDCl 3 , 400MHZ): 1.16, 1.24, 1.26, 1.35, 1.38, 1.40, 1.41, 1.49, 1.52, 1.60, 1.63, 1.88, 1.91, 2.01, 2.29, 2.35, 2.89, 3.16, 5.85.

Embodiment 3

[0046] According to the method of Example 1, 11β, 17α, 21-trihydroxypregna-1,4-diene-3,20-dione was used to react with triethyl orthoacetate to obtain 11β, 17α, 21-trihydroxypregna -1,4-diene-3,20-dione-17-acetate white powder 55.8g, yield 96.5%.

[0047] Melting point: 162-166°C

[0048] 1 H-NMR (CDCl 3 , 400MHZ): 1.12, 1.14, 1.16, 1.35, 1.36, 1.38, 1.40, 1.41, 1.56, 1.60, 1.61, 1.87, 1.91, 2.01, 2.12, 2.29, 3.26, 4.69, 6.09, 6.28, 6.34.

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Abstract

The invention discloses a preparation method of a steroid, and particularly relates to a preparation method of 17 alpha-hydroxyl steroid ester. 17 alpha, 21-dyhydroxyl steroid reacts with orthoester to form a steroid intermediate containing 1, 3-dioxane-5-cyclohexanone, and then 17 alpha-hydroxyl steroid ester is obtained through hydrolysis. Compared with the prior art, the preparation method has the advantages that highly amyctic trifluoroacetic anhydride is avoided, the reaction condition is mild, a solid acid can be adopted for catalytic hydrolysis, the catalytic acid is recycled, so that environmental protection is facilitated, and the method has low pollution, simple technology and mild reaction condition, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a steroid compound, in particular to a preparation method of a 17α-hydroxy steroid ester. Background technique [0002] The 17α-hydroxyl esterification of steroids is an important reaction of steroids. Esterification can improve the ester solubility of steroidal drugs, and then improve the transdermal absorption rate of such drugs, such as hydrocortisone butyrate, betamethasone dipropionate, etc.; after esterification, a series of follow-up Reaction, such as 17α-dehydroxylation reaction in the preparation process of ciclesonide, halcinonide, desononide, budesonide, etc. [0003] Michael J.Green, et al. use trifluoroacetic anhydride to carry out esterification (J.Med.Chem., 25,1492-1495,1982), the trifluoroacetic anhydride used in this method has volatility, irritation, in There are limitations in industrial production. [0004] During the hydrolysis process of the 1,3-dioxan-5-one ring of the compound...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00C07J75/00
Inventor 骆均勇陶长戈
Owner CHENGDU YILUKANG MEDICAL TECH & SERVICE
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