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Preparation method of 17hydroxy-pregnane-4-alkene-3,20-diketone-21-acetic ester

A technology of acetate and pregnan, which is applied in the field of preparation of 17-hydroxy-pregn-4-ene-3,20-dione-21-acetate, can solve the problems of low yield and high cost, and achieves a high yield High, stable yield and wide-ranging effects

Inactive Publication Date: 2014-06-04
ZHEJIANG XIANJU JUNYE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The present invention proposes a preparation method of 17-hydroxy-pregna-4-ene-3,20-dione-21-acetate, which solves the problems of low yield and high cost in the prior art

Method used

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  • Preparation method of 17hydroxy-pregnane-4-alkene-3,20-diketone-21-acetic ester
  • Preparation method of 17hydroxy-pregnane-4-alkene-3,20-diketone-21-acetic ester
  • Preparation method of 17hydroxy-pregnane-4-alkene-3,20-diketone-21-acetic ester

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Experimental program
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Effect test

Embodiment 1

[0033] The reaction scheme of the present invention is as follows:

[0034]

[0035] Cyanation reaction

[0036] Put 100 milliliters of methanol, 50 grams of acetone cyanohydrin, and 100 grams of the compound represented by formula (II) into a three-necked flask. Turn on the stirring and slowly raise the temperature to 35°C. The prepared potassium carbonate solution was slowly added dropwise, and the temperature was controlled at 32° C. for 20 h. TLC detection confirmed that the raw material point is very small and the raw material point is no longer reduced, then cooled to 5°C, slowly passed the material into a beaker of 2 liters of water that had been cooled to below 10°C in advance, and stood still for more than 2h. Filter and wash with water until neutral. Add the filter cake to the prepared dilute hydrochloric acid, stir for 2 hours, filter, wash the filter cake with a large amount of water until PH = 6.0-6.5, filter, and discharge. The filter cake was transferred ...

Embodiment 2

[0044] Cyanation reaction

[0045] Put 100 milliliters of ethanol, 100 grams of sodium cyanide, and 100 grams of the compound represented by formula (II) into a three-necked flask. Turn on the stirring and slowly raise the temperature to 38°C. The prepared sodium hydroxide solution was slowly added dropwise, and the temperature was controlled at 38° C. for 20 h. TLC detection confirmed that the raw material point is very small and the raw material point is no longer reduced, then cooled to 0 °C, slowly passed the material into a beaker of 2 liters of water that had been cooled to below 10 °C in advance, and stood still for more than 2 hours. Filter and wash with water until neutral. Add the filter cake to the prepared dilute hydrochloric acid, stir for 2 hours, filter, wash the filter cake with a large amount of water until PH = 6.5, filter, and discharge. The filter cake was transferred to an oven and dried at 72°C for 12h. In crude cyanide. The yield is about 97%, HPLC≥...

Embodiment 3

[0053] Cyanation reaction

[0054] Put 100 milliliters of acetone, 70 grams of potassium cyanide, and 100 grams of the compound represented by formula (II) into a three-necked flask. Turn on the stirring and slowly raise the temperature to 50°C. The prepared sodium carbonate solution was slowly added dropwise, and the temperature was controlled at 50°C for 18 hours. TLC detection confirmed that the raw material point is very small and the raw material point is no longer reduced, then cooled to 0 °C, slowly passed the material into a beaker of 2 liters of water that had been cooled to below 10 °C in advance, and stood still for more than 2 hours. Filter and wash with water until neutral. Add the filter cake to the prepared dilute hydrochloric acid, stir for 2 hours, filter, wash the filter cake with a large amount of water until PH = 6.5, filter, and discharge. The filter cake was transferred to an oven and dried at 70°C for 12h. In crude cyanide. The yield is about 96%, H...

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Abstract

The invention provides a preparation method of a 17hydroxy-pregnane-4-alkene-3, 20-diketone-21-acetic ester. The preparation method is characterized in that a compound as shown in a formula (II) described in the specification is subjected to cyanation, protection, nucleophilic substitution and esterification reaction, and the 17hydroxy-pregnane-4-alkene-3, 20-diketone-21-acetic ester as shown in the formula (I) is obtained. The preparation method provided by the invention has the advantages that the process is simple, the cost is low, the yield is high and stable, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of 17-hydroxy-pregna-4-ene-3,20-dione-21-acetate. Background technique [0002] In the prior art, 17α-hydroxyprogesterone is obtained through two methods, and then 17hydroxy-pregna-4-ene-3,20-dione-21-acetate is obtained through iodine addition and displacement reaction. [0003] [0004] The two ways to obtain 17α-hydroxyprogesterone are: [0005] A: With 11a-hydroxy-16,17a-epoxyprogesterone (mycotic oxide) as the starting material, it undergoes ring-opening and debromination reactions: [0006] [0007] B: Using 1,4-androstene-3,20-dione (4-AD) as the starting material, through cyanation, ketal protection, and Grignard reaction: [0008] [0009] The above preparation methods have the following deficiencies: all need to use iodine, which increases the cost; approach A takes the fungal oxide as the starting raw material, and because of ...

Claims

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Application Information

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IPC IPC(8): C07J5/00
Inventor 张峥斌王润田胡明辉王锦凯
Owner ZHEJIANG XIANJU JUNYE PHARM CO LTD
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