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Synthesis process of methyl prednisolone aceponate

A technology of methylprednisolone and dragon vinegar propionate, applied in the direction of steroids, organic chemistry, etc., can solve the problems of high industrialization cost, poor product purity, and poor catalytic effect, and achieve reaction yield High efficiency, high product purity, and easy industrialization

Inactive Publication Date: 2008-12-03
TAIZHOU TAIFA PHARMA
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  • Description
  • Claims
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Problems solved by technology

[0004] However, in this method, oxalic acid is used as a catalyst in the cyclic ester hydrolysis process product yield is relatively low, which makes the industrialization cost of this technology high. In addition, because the catalytic effect is not good, some by-products of cyclic ester hydrolysis will bring the next step of acetic acidification reaction. It has a great impact, so that the total yield of propionation, cyclic ester hydrolysis and acetic acidification is only 58%, and the purity of the final product is not good. To obtain a high-purity product, a purification method with a large loss must be adopted

Method used

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  • Synthesis process of methyl prednisolone aceponate
  • Synthesis process of methyl prednisolone aceponate

Examples

Experimental program
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Effect test

Embodiment 1

[0023] (1) Propionation

[0024] Weigh 10g of methylprednisolone, add 12g of triethyl orthopropionate, 35ml of dimethylformamide, 4g of p-toluenesulfonic acid, react at 60-80°C for 5h, add 300ml of ethyl acetate and 3% carbonic acid 200ml of sodium hydrogen solution, stirred for 30 minutes, separated into layers, washed with water until neutral, concentrated to dryness under reduced pressure, added 20ml of methanol for secondary concentration to dryness, added 300ml of water, stirred for 30 minutes, filtered, washed with water until neutral to obtain a cyclic ester intermediate.

[0025] (2) Cyclic ester hydrolysis

[0026] Add 10g of cyclic ester intermediate, 400ml of methanol, 4g of silica gel, reflux for 4.5 hours, filter, concentrate under reduced pressure, leave about 10g of mother liquor, add 300ml of water for analysis, stir for 30 minutes, filter, wash with water until neutral to obtain a hydrolyzate (propionic acid methylprednisolone) and dried.

[0027] (3) Acetif...

Embodiment 2

[0030] (1) Propionation

[0031] Weigh 20g of methylprednisolone, add 24g of triethyl orthopropionate, 70ml of dimethylformamide, 8g of p-toluenesulfonic acid, react at 75°C for 4.5h, add 600ml of ethyl acetate and 3% sodium bicarbonate The solution was 250ml, stirred for 30 minutes, separated into layers, washed with water until neutral, concentrated to dryness under reduced pressure, added 45ml of methanol for a second concentration to dryness, added 600ml of water, stirred for 30 minutes, filtered, washed with water until neutral to obtain a cyclic ester intermediate.

[0032] (2) Cyclic ester hydrolysis

[0033] Add 5g of cyclic ester intermediate, 240ml of methanol, 1.5g of silica gel, reflux for 6 hours, filter, concentrate under reduced pressure, leave about 5g of mother liquor, add 400ml of water for analysis, stir for 40 minutes, filter, wash with water until neutral to obtain a hydrolyzate (A acid methylprednisolone) and dried.

[0034] (3) Acetification

[0035] ...

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Abstract

The present invention relates to synthesis process of methyl prednisolone aceponate. The synthesis process of methyl prednisolone aceponate adopts methyl prednisolone as initial material, and includes reaction with propionic acid, cyclic ester hydrolysis under the catalysis of 200-300 mesh G-type silica gel as catalyst, and reaction with acetic acid. The synthesis process of the present invention can obtain methyl prednisolone aceponate product of purity over 98 %, has less side products, and is simple, mild in reaction condition and easy use in industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing methylprednisolone propionate, which uses methylprednisolone as a starting material. Background technique [0002] Methylprednisolone propionate is an important intermediate of hormone APIs. [0003] In the U.S. invention patent US4567172, a kind of synthetic method of methylprednisolone acetate propionate is disclosed. The method takes methylprednisolone as starting material through three steps of propionation, cyclic ester hydrolysis and acetic acidification, Using oxalic acid as a catalyst in the hydrolysis of cyclic esters, [0004] However, in this method, oxalic acid is used as a catalyst in the cyclic ester hydrolysis process product yield is relatively low, which makes the industrialization cost of this technology high. In addition, because the catalytic effect is not good, some by-products of cyclic ester hydrolysis will bring the next step of acetic acidification reaction. Very big influenc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J5/00
Inventor 汪家振
Owner TAIZHOU TAIFA PHARMA
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