A synthetic method of 17alpha-hydroxy-17beta-cyano-steroid compounds

A technology of steroidal compounds and synthetic methods, which is applied in the field of synthesis of 17αhydroxyl-17βnitrile-steroidal compounds, can solve problems such as incomplete reaction and long reaction time, and achieve product quality improvement, quality and yield improvement, The effect of solving environmental problems

Inactive Publication Date: 2018-04-10
ZHEJIANG XIANJU JUNYE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] To sum up, according to the traditional process, the product accounts for about 88-90%, the by-products 1 and 2 account for about 5% respectively, and 1-2% of the raw materials are not completely reacted, and the reaction time is more than 30h

Method used

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  • A synthetic method of 17alpha-hydroxy-17beta-cyano-steroid compounds
  • A synthetic method of 17alpha-hydroxy-17beta-cyano-steroid compounds
  • A synthetic method of 17alpha-hydroxy-17beta-cyano-steroid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Take a three-necked reaction flask, add 100g of compound (I-1), add 90g of methanol, heat up to 30-32°C, add 1g of 3-butene-2-ketone, then add 80g of acetone cyanohydrin and stir for 3min, add the prepared 3 % potassium carbonate aqueous solution 200ml. Insulated for 30 hours, the raw materials were basically completely reacted by sampling. After cooling down to 0-5°C, stir for 30 minutes. Suction filtration, wash the filter cake with a small amount of water until neutral, and dry to obtain 104.9 g of the product, with a mass yield of 104.9%. HPLC content: compound (II-1) 98.2%, compound (III-1) 0.8%, compound (IV-1) 0.5%.

Embodiment 2

[0025]

[0026] Take a three-necked reaction flask, add 100g of compound (I-2), add 100g of methanol, heat up to 29-31°C, add 1g of 3-butene-2 ​​ketone, then add 80g of acetone cyanohydrin and stir for 3min, add dropwise 3% 200ml of sodium carbonate aqueous solution. Insulated for 32 hours, the raw materials were basically completely reacted by sampling. After cooling down to 0-5°C, stir for 30 minutes. Suction filtration, wash the filter cake with a small amount of water until neutral, and dry to obtain 105.1 g of the product, with a mass yield of 105.1%. HPLC content: compound (II-2) 98.4%, compound (III-1) 0.6%, compound (IV-1) 0.5%.

Embodiment 3

[0028]

[0029] Take a three-necked reaction flask, add 100g of compound (I-3), add 110g of methanol, heat up to 32-33°C, add 1g of 3-buten-2-ketone, then add 90g of acetone cyanohydrin and stir for 3min, add the prepared 3% 200ml of sodium carbonate aqueous solution. Insulated for 31 hours, the raw materials were basically completely reacted by sampling. After cooling down to 0-5°C, stir for 30 minutes. Suction filtration, wash the filter cake with a small amount of water until neutral, and dry to obtain 105.3 g of the product, with a mass yield of 105.3%. HPLC content: compound (II-3) 98.3%, compound (III-3): 0.7%, compound (IV-3) 0.4%.

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PUM

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Abstract

A synthetic method of 17alpha-hydroxy-17beta-cyano-steroid compounds is disclosed. The method includes a) dispersing a compound of a formula (I) into methanol, heating the mixture to 30-32 DEG C, adding 3-buten-2-one into the mixture, then adding acetone cyanohydrin into the mixture, fully stirring the mixture, then adding dropwise a prepared aqueous potassium carbonate solution, and maintaining the temperature until the reaction is completed; and 2) cooling the reaction solution to 0-5 DEG C after the reaction is finished, then stirring the reaction solution until a product is completely precipitated, performing suction filtration, washing filter cake with a small amount of water until neutrality, and drying the product to obtain a compound of a formula (II), and a small amount of a compound of a formula (III) and a compound of a formula (IV) which are adopted as byproducts. The weight ratio of the compound of the formula (I), the methanol, the 3-buten-2-one and the acetone cyanohydrin is 100:90-110:0.9-1.1:80-90. The weight-to-volume ratio of the compound of the formula (I) to the potassium carbonate solution is 100:90-110. The weight percentage of the potassium carbonate solution is 2.5-3.5%.

Description

technical field [0001] The invention relates to a method for synthesizing 17α hydroxyl-17β nitrile-steroid compound. Background technique [0002] The traditional preparation of steroid hormones needs to use diosgenin as a raw material, but due to the serious pollution of the saponin industry, sterols are gradually used as starting materials in the synthesis of steroid hormones. The process of ene (5,16-pregna-3β-ol-20-keto-3-acetate) as the starting material is gradually replaced by a new synthetic route from sterol via 4AD, 9α-OH-4AD, etc. replaced. When 4AD and 9α-OH-4AD are used as raw materials to prepare steroid drugs, the introduction of the 17-position side chain needs to be cyanohydrinated by the 17-position ketone group to obtain the 17α hydroxyl-17β nitrile-steroid compound, and then undergo Grignard reaction . The existing industrialized production of 17α hydroxy-17β nitrile-steroid compounds is basically a methanol-water system, acetone cyanohydrin is the cya...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
CPCC07J41/0094
Inventor 徐思虎吴孝凯胡明辉
Owner ZHEJIANG XIANJU JUNYE PHARM CO LTD
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