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About a kind of preparation method of pregna-16-ene-3,20-dione steroid derivative

A technology of diketone steroids and derivatives, which is applied in the field of steroid synthesis, can solve the problems of being unsuitable for industrial production, cumbersome, difficult to refine, etc., and achieve the effects of environmental protection and cost reduction

Active Publication Date: 2017-11-07
TIANJIN JINYAO GRP
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction has many steps and is cumbersome
[0023] The method for preparing the pregna-16-ene-3,20-dione steroid derivative (II) using the 17α-ethynyl-17β-hydroxy steroid compound (I) as the starting material has low yield and many impurities , not easy to refine, some need to be purified by chromatographic column, some also use the rare metal ruthenium, the cost is high, these methods are currently only at the laboratory level, and there are no reports of industrialization
Through repeated experiments, we found that these methods are not suitable for industrial production due to the above-mentioned problems such as low yield, many impurities, and high cost.

Method used

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  • About a kind of preparation method of pregna-16-ene-3,20-dione steroid derivative
  • About a kind of preparation method of pregna-16-ene-3,20-dione steroid derivative
  • About a kind of preparation method of pregna-16-ene-3,20-dione steroid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0044] Put 700L of carbon tetrachloride into a clean and dry 1000L reaction tank, then add 6.63kg of 15% phosphorus pentoxide-methanesulfonic acid and stir well at room temperature. Then, 3.28 Kg of 11β-hydroxy-17α-ethynyl-17β-hydroxy-4-ene-androst-3-one was added. Steam was heated to 60°C, and the reaction was timed for 1h. TLC detected that the raw material disappeared, cooled to room temperature and filtered, concentrated the filtrate to nearly dryness, rinsed with 500 L of ice water, stirred and cooled to room temperature. Throw material. 2.79 Kg of 11β-hydroxy-4,16-diene-pregna-3,20-dione was obtained with a molar yield of 85% and an HPLC content of 90%.

Embodiment 1-2

[0046] Put 700L of carbon tetrachloride into a clean and dry 1000L reaction tank, then add 6.17kg of 7% phosphorus pentoxide-methanesulfonic acid and stir well at room temperature. Then, 3.28 Kg of 11β-hydroxy-17α-ethynyl-17β-hydroxy-4-ene-androst-3-one was added. Heat the steam to 60°C, and time the reaction for 2h. TLC detected the disappearance of the raw material, cooled to room temperature and filtered, concentrated the filtrate to nearly dryness, rinsed with 300 L of ice water, stirred and cooled to room temperature. Throw material. 2.95 Kg of 11β-hydroxy-4,16-diene-pregna-3,20-dione was obtained with a molar yield of 90% and an HPLC content of 93%.

Embodiment 1-3

[0048] Put 700L of carbon tetrachloride into a clean and dry 1000L reaction tank, then add 6.05kg of 5% phosphorus pentoxide-methanesulfonic acid and stir well at room temperature. Then, 3.28 Kg of 11β-hydroxy-17α-ethynyl-17β-hydroxy-4-ene-androst-3-one was added. Steam was heated to 60°C, and the reaction was timed for 1h. TLC detected that the raw material disappeared, cooled to room temperature and filtered, concentrated the filtrate to nearly dryness, rinsed with 500 L of ice water, stirred and cooled to room temperature. Throw material. 2.79Kg of 11β-hydroxy-4,16-diene-pregna-3,20-dione was obtained with a molar yield of 85% and an HPLC content of 89%.

[0049] Example 2 Preparation of 11α-hydroxy-4,16-diene-pregna-3,20- Diketone, the content of starter is 93% in the present embodiment.

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Abstract

The invention relates to a preparation method for a pregna-16-ene-3, 20-dione steroid derivative (II). The method is characterized by: reacting 17alpha-ethynyl-17beta-hydroxysteroid derivative I with a reagent A or an organic solvent containing the reagent A to obtaining the derivative (II). The reaction temperature ranges from 25DEG C to a solvent reflux temperature, and the reagent A is a solution formed by dissolving 5%-15% of phosphorus pentoxide in methanesulfonic acid.

Description

technical field [0001] The invention belongs to the technical field of steroid synthesis and relates to the preparation of pregna-16-ene-3,20-dione steroid derivatives from 17α-ethynyl-17β-hydroxy steroid derivatives. Background technique [0002] Pregna-4,16-diene-3,20-dione and its derivatives are key intermediates in the synthesis of steroids, used in the manufacture of dexamethasone, betamethasone, methylprednisolone, and hydrocortisone , prednisone and other steroid drugs have high economic value. Now the common method for industrial production of pregna-4,16-diene-3,20-dione and its derivatives is to use pregna-5,16-diene-20-one-3-hydroxyl-3-acetate (referred to as diene) as raw material preparation. Dienes are produced from diosgenin through three steps of cracking, oxidation, and hydrolysis. First, this production process requires a large amount of sulfuric acid, which is likely to cause a lot of pollution to the environment; second, with the continuous improvement...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J13/00C07J75/00
CPCC07J13/005C07J75/00
Inventor 卢彦昌王淑丽孙亮
Owner TIANJIN JINYAO GRP
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