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Preparation method for hydrocortisone intermediate

A technology of hydrocortisone and intermediates, applied in the field of chemical synthesis of steroid hormone drugs, can solve the problems of high production requirements, high process cost, long synthesis steps, etc., to reduce the dependence of high-end equipment and achieve high yield , the effect of short synthesis steps

Active Publication Date: 2014-03-19
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This preparation method has long synthesis steps and low yield. The reaction also involves dangerous operations such as bromine addition and hydrogenation, which has high requirements for production. At the same time, the reaction involves high-cost operations such as iodine addition, and the process cost is relatively high.

Method used

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  • Preparation method for hydrocortisone intermediate
  • Preparation method for hydrocortisone intermediate
  • Preparation method for hydrocortisone intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Cyano substitution reaction

[0021] At room temperature, add 200ml of methanol, 100ml of acetone cyanohydrin, and 200.0g of compound I to a clean and dry 2000ml four-necked round-bottomed flask equipped with a thermometer, reflux condenser, and mechanical stirring. After stirring evenly, add 200ml of Potassium carbonate aqueous solution, the temperature of the system was controlled at 40-50° C. for 30 hours, and TLC detected that the raw materials were no longer reduced. The reaction system was added dropwise to 4000ml of water and stirred for 2 hours. Suction filtration, washing the filter cake with water to neutrality, and drying at 50°C to obtain 210 g of compound II with a yield of 105% and a HPLC purity of 97.8%.

[0022] Siloxyl Protection Reaction

[0023] At room temperature, add 250ml of chloroform, 100.0g of compound II, and 52g of imidazole to a clean and dry 2000ml four-necked round-bottom flask equipped with a thermometer, reflux condenser, and mechanica...

Embodiment 2

[0029] Cyano substitution reaction

[0030] At room temperature, add 300ml of acetone, 120g of acetone cyanohydrin, and 200.0g of compound I to a clean and dry 2000ml four-necked round-bottom flask equipped with a thermometer, reflux condenser, and mechanical stirring. After stirring evenly, add 150ml of sodium carbonate solution, the temperature of the system was controlled at 40-50° C. for 20 hours, and TLC detected that the raw materials were no longer reduced. 1000 ml of water was added dropwise to the reaction system, and stirred for 2 hours. Suction filtration, washing the filter cake with water to neutrality, and drying at 50°C to obtain 208g of compound II, yield: 104%, HPLC purity 97.5%.

[0031] Siloxyl Protection Reaction

[0032] At room temperature, add 600ml of toluene, 100g of compound II, and 54g of triethylamine to a clean and dry 2000ml four-necked round-bottomed flask equipped with a thermometer, reflux condenser, and mechanical stirring in sequence. After...

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Abstract

The invention relates to a preparation method of a hydrocortisone intermediate, which is prepared from a compound I by means of cyanogroup substitution reaction, siloxy protective reaction, intramolecular nucleophilic substitution reaction and replacement reaction. The method provided by the invention has the advantages of high yield and low cost, and the reaction route is shown as the specification.

Description

technical field [0001] The invention relates to a chemical synthesis method of a steroid hormone drug, in particular to a preparation method of a hydrocortisone intermediate. Background technique [0002] Hydrocortisone, as the most produced variety of steroidal corticosteroids, is widely used in the treatment of adrenal insufficiency and autoimmune diseases. my country's steroid drug and its intermediate industry has reached a certain scale, and it has become the largest exporter of hydrocortisone and prednisolone in the world. At present, the synthesis of hydrocortisone is mainly made by the combination of biological fermentation and chemical synthesis of RSA. [0003] The preparation of the compound cortisone acetate is currently produced by the vast majority of manufacturers according to the RSA process of hydrocortisone intermediate in the "National Compilation of Raw Materials Processes" (State Administration of Medicine, 1980). Part of the process describes the comp...

Claims

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Application Information

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IPC IPC(8): C07J5/00
Inventor 刘喜荣
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD
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