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One-step method for synthesizing halometasone from diclomethasone ethyl ester

A technology of diclomethasone ethyl ester and halometasone, applied in the direction of steroids, organic chemistry, etc., can solve the problems of unfavorable industrial production, endangering people's health, cumbersome processing process, etc., and achieve low cost and high yield High, simple method and effective effect

Active Publication Date: 2016-03-02
HUNAN MINGRUI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

According to experiments, this method uses pyridine in the process of synthesizing halometasone, and the follow-up process is cumbersome. Pyridine is extremely harmful to human health and is not conducive to industrial production.

Method used

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  • One-step method for synthesizing halometasone from diclomethasone ethyl ester

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Experimental program
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Embodiment 1

[0031] Embodiment 1: the synthesis of halometasone

[0032] Synthesize halometasone according to the patent document US3652554, take 10g of diclomethasone ethyl ester, dechlorinate with pyridine, and hydrolyze with aqueous sodium bicarbonate solution, 6.9g, yield: 78.01%, purity: 90.32%

Embodiment 2

[0033] Embodiment 2: the synthesis of halometasone

[0034] Take 10.0g of diclomethasone ethyl ester and add it to a 500ml reaction bottle, then add 100.0g of methanol, blow nitrogen into it and stir to dissolve it, drive out all the air in about 10 minutes, and slowly add 10 10.6g of % sodium hydroxide aqueous solution, about 15 minutes to complete the dropwise addition, temperature control 0-10 ℃ to continue the reaction, TLC detection, about 4.5h to complete the reaction, after the reaction is completed, use glacial acetic acid to control the pH at 6-7, drop quickly Purified water 50.0g, continue temperature control 0-10°C to crystallize for 1h, filter, wash with purified water 20g / time for three times, and vacuum dry at 45°C for 20h to obtain 8.1g light yellow solid powder, yield 91.69%, product structure identification data as follows:

[0035] ESI: molecular ion peak [M+Na] + for 467.1

[0036] H-NMR (δppm): 7.565, 7.567 (d, 1H), 6.224 (s, 1H), 5.610-5.638, 5.691-5.71...

Embodiment 3

[0038] Embodiment 3: the synthesis of halometasone

[0039] Take 10.0g of diclomethasone ethyl ester and add it to a 500ml reaction bottle, then add 100.0g of methanol, blow nitrogen into it and stir to dissolve it, drive out all the air in about 10 minutes, and slowly add 10 % Potassium hydroxide aqueous solution 14.8g, about 15 minutes to complete the dropwise addition, temperature control 0-10 ℃ to continue the reaction, TLC detection, about 4.5h to complete the reaction, after the reaction is completed, use glacial acetic acid to control the pH at 6-7, quickly add dropwise Purified water 50.0g, continue to crystallize at 0-10°C for 1h, filter, wash with purified water 20g / time for three times, and vacuum dry at 45°C for 20h to obtain 7.2g light yellow solid powder, yield 92.72%

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Abstract

The invention discloses a method for synthesizing halometasone from ethyl dichloroflumethasone by one step. Under the condition that inert gas is introduced, ethyl dichloroflumethasone which is taken as a raw material reacts with methanol which is taken as a solvent by one step to obtain halometasone under the action of alkali. According to the method, operation steps are simplified, the yield is increased, and the use of a toxic and harmful solvent is reduced.

Description

technical field [0001] The invention relates to a method for synthesizing halometasone. Background technique [0002] Clomethasone ethyl ester is an important intermediate in the synthetic dermatological drug "halometasone". After hydrolysis of cloflumethasone ethyl ester, halometasone can be obtained. [0003] Patent document US3652554 has reported the method for synthesizing halometasone from flumethasone ethyl ester, and it adopts the chlorination of flumetasone ethyl ester to generate diclomethasone ethyl ester, and diclomethasone ethyl ester generates monoclomethasone ethyl ester through pyridine dechlorination, Then a cloflumethasone ethyl ester is hydrolyzed by aqueous sodium bicarbonate to generate halometasone. According to experiments, this method uses pyridine in the process of synthesizing halometasone, and the follow-up treatment process is cumbersome. Pyridine is extremely harmful to human health and is not conducive to industrial production. [0004] Finding...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J5/00
CPCC07J5/0076
Inventor 蔡辉刘爱民易申赢叶凯
Owner HUNAN MINGRUI PHARMA
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