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Method for preparing methylprednisolone

A technology of methylprednisolone and dichloromethane, applied in the field of chemical preparation, can solve the problems of high price, complicated process, cumbersome steps and the like, and achieve the effects of low cost, good selectivity and simple reaction

Inactive Publication Date: 2017-11-10
ZHEJIANG XIANJU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The purpose of the present invention is to solve the technical problem that the current production process of methylprednisolone uses mold dehydrogenation as raw material or key intermediate, which is expensive, complicated in process and cumbersome in steps

Method used

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  • Method for preparing methylprednisolone
  • Method for preparing methylprednisolone
  • Method for preparing methylprednisolone

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Experimental program
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Effect test

Embodiment 1

[0047] The first step, ketal protection reaction: dissolve hydrocortisone 1 (10g, 1W) in dichloromethane (200mL, 20V), add formaldehyde aqueous solution (100mL, 10V) under stirring, slowly add concentrated hydrochloric acid (100ml, 10V ), stirred at room temperature for 8 hours, TLC detected no raw material point, stopped the reaction, separated the organic phase, extracted the aqueous phase with dichloromethane, and combined the organic phases. The organic phase was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The organic solvent was removed by rotary evaporation under reduced pressure to obtain a mixture of protected products 2a and 2b (11.02g, 110%), product 2a HPLC (240nm, 55%), and product 2b HPLC (240nm, 37%).

[0048] The second step, methylation reaction: Add sodium acetate (20g, 2W), dichloromethane (100mL, 10V) and methylal (200mL, 20V) into the react...

Embodiment 2

[0055] The first step, ketal protection reaction: dissolve hydrocortisone 1 (10g, 1W) in dichloromethane (100mL, 10V), add formaldehyde aqueous solution (46mL, 4.6V) under stirring, slowly add concentrated hydrochloric acid (42ml, 4.2V), stirred at 30°C for 10 hours, stopped the reaction, separated the organic phase, extracted the aqueous phase with dichloromethane, and combined the organic phases. The organic phase was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The organic solvent was removed by rotary evaporation under reduced pressure to obtain a mixture of protected products 2a and 2b (10.4g, 104%), product 2a HPLC (240nm, 30%), product 2b HPLC (240nm, 40%).

[0056] Other steps are with embodiment 1.

Embodiment 3

[0058] The first step, ketal protection reaction: dissolve hydrocortisone 1 (10g, 1W) in dichloromethane (400mL, 40V), add formaldehyde aqueous solution (185mL, 18.5V) under stirring, slowly add concentrated hydrochloric acid (170ml, 17V), stirred at 20°C for 6 hours, stopped the reaction, separated the organic phase, extracted the aqueous phase with dichloromethane, and combined the organic phases. The organic phase was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The organic solvent was removed by rotary evaporation under reduced pressure to obtain a mixture of protected products 2a and 2b (111g, 111%), product 2a HPLC (240nm, 50%), and product 2b HPLC (240nm, 43%).

[0059] Other steps are with embodiment 2.

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Abstract

The invention discloses a method for preparing methylprednisolone. Hydrocortisone serves as the raw material, a hydroxyl group is protected through ketalation, six methyl groups are introduced through methylene reaction and catalytic hydrogenation, 6 alpha-methyl hydrocortisone is obtained through hydrolysis deprotection, and methylprednisolone is obtained through biodehydrogenation, wherein the equation is shown in the description. Hydrocortisone serves as the initial raw material, through five-step reaction, methylprednisolone is obtained with the total weight yield of 60% or above, reaction is simple, selectivity is good, and methylprednisolone is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing chemicals, in particular to a method for preparing methylprednisolone. Background technique [0002] Methylprednisolone belongs to the class of glucocorticoids and is used for emergency treatment of critical illnesses. It can also be used for endocrine disorders, rheumatic diseases, collagen venereal diseases, skin diseases, allergic reactions, eye diseases, gastrointestinal diseases, blood diseases, Leukemia, shock, cerebral edema, polyneuritis, myelitis, and prevention of vomiting caused by cancer chemotherapy. At present, it is mainly used clinically for organ transplantation. [0003] Invention patent CN 1763066A discloses that pregnane dienolone acetate is used as a starting material, and after epoxidation, Woerg reaction, mold reaction, Platts reaction, debromination, iodine replacement, 11-position reduction reaction, 1- 2 dehydrogenation reaction, 6-methylation, hydrolysis to obtain methylpredni...

Claims

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Application Information

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IPC IPC(8): C12P33/02C12R1/06
CPCC12P33/02
Inventor 戴静刘建
Owner ZHEJIANG XIANJU PHARMA
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