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Method for the synthesis and purification of 25-hydroxycholesterol

A hydroxycholesterol, addition technology, applied in the directions of organic chemistry, steroids, etc., can solve the problems of unobtainable raw materials, complicated preparation process, etc., and achieve the effects of reducing production cost, simple process, and mild addition reaction conditions.

Active Publication Date: 2022-04-05
江西天新药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The purpose of the present invention is to provide a method for preparing 25-hydroxycholesterol in order to overcome the technical problems in the prior art that the raw materials are not easy to obtain, the preparation process is complicated and there are potential safety hazards. The method has the advantages of easy to obtain raw materials, simple process steps, and safety High coefficient and other advantages, but also conducive to the realization of industrialization

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  • Method for the synthesis and purification of 25-hydroxycholesterol
  • Method for the synthesis and purification of 25-hydroxycholesterol
  • Method for the synthesis and purification of 25-hydroxycholesterol

Examples

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Embodiment 1

[0064] Add 42.6g of the mixture (external standard content: the content of 24-dehydrocholesterol acetyl ester is 31.3wt% (13.3g, 31.4mmol), the content of cholesterol acetyl ester is 67.6wt%) to a 10L three-necked flask, and use 500mL Dissolve the above mixture in xylene, and then add 4500 g (50 mol) of lactic acid dropwise under stirring. It takes 0.5 h to complete the dropping, and after the addition reaction at 55 ° C for 5 h under stirring, the HPLC traces the reaction until the 24-dehydrocholesterol acetyl ester no longer decreases; 55 Under the condition of ℃, extract the reaction solution after the above-mentioned addition reaction with n-octane (1000mL×2 times), and separate the layers to obtain the n-octane phase and the remaining acid phase, wherein the remaining acid phase can continue to be used for the addition reaction. The n-octane phases obtained by the two extractions were combined, and then evaporated to dryness to obtain 45.1 g of the adduct, and 11.2 g (200 ...

Embodiment 2

[0068] Add 42.6g of the mixture (external standard content: the content of 24-dehydrocholesterol acetyl ester is 31.3wt% (13.3g, 31.4mmol), the content of cholesterol acetyl ester is 67.6wt%) to a 10L three-necked flask, and use 500mL Dissolve the above mixture in xylene, then add 3600 g (40 mol) of acetic acid dropwise under stirring, and it takes 0.5 h to finish the dropping. After the addition reaction under stirring at 100° C. for 4 h, HPLC tracks the reaction until 24-dehydrocholesteryl acetyl ester no longer decreases; 100 Under the condition of ℃, extract the reaction solution after the above-mentioned addition reaction with n-octane (1000mL×2 times), and separate the layers to obtain the n-octane phase and the remaining acid phase, wherein the remaining acid phase can continue to be used for the addition reaction. The n-octane phases obtained by the two extractions were combined, and then evaporated to dryness to obtain 44.8 g of the adduct, and 11.2 g (200 mmol) of pot...

Embodiment 3

[0071] Add mixture 42.6g (external standard content: the content of 24-dehydrocholesterol acetyl ester is 31.3wt% (13.3g, 31.4mmol), the content of cholesterol acetyl ester is 67.6wt%) in the three-neck flask of 5L), and use 500mL Dissolve the above mixture in 1,2-dichloroethane, and then add 1380g (30mol) of formic acid dropwise with stirring. It takes 0.5h to complete the dropwise addition reaction at 60°C for 4h, and follow the reaction by HPLC until 24-dehydrocholesteryl acetyl ester no longer decrease; under the condition of 60°C, extract the reaction solution of the above addition reaction with petroleum ether (1000mL×2 times), and separate the layers to obtain the petroleum ether phase and the remaining acid phase, wherein the remaining acid phase can continue to be used for the addition reaction , combined the petroleum ether phases obtained by the two extractions, and then evaporated to dryness to obtain 44.0 g of the adduct, and added 11.2 g (200 mmol) of potassium hy...

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Abstract

The present invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing and purifying 25-hydroxycholesterol, comprising the following steps: (1) mixing the mixture containing the compound shown in formula (I) and the compound shown in formula (II) with The addition reagent is contacted to obtain an addition product; wherein, based on the total weight of the mixture, the content of the compound represented by the formula (I) is 10-60wt%; the addition reagent has the formula (III) Structure shown; In formula (I) and formula (II), R 1 Be the acyl group of H or C1-C4; In formula (III), R 2 is C1‑C4 acyl; and, R 1 and R 2 The same or different; (2) saponifying the addition product with an alkali to obtain a saponification product; then obtaining 25-hydroxycholesterol through crystallization and separation. The method for preparing 25-hydroxycholesterol provided by the invention has the advantages of easy-to-obtain raw materials, simple and safe process steps.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing and purifying 25-hydroxycholesterol. Background technique [0002] 25-hydroxyvitamin D3 has wide application prospects and high economic value. 25-hydroxycholesterol is an important raw material for the synthesis of 25-hydroxyvitamin D3. Existing methods for preparing 25-hydroxycholesterol generally include the following methods, for example: [0003] (a) Hydroxymercury method [0004] [0005] This method (C.R.Chimie, 6, 79-82, 2003) uses 24-dehydrocholesterol (or derivatives) as raw material, uses mercury acetate to do hydroxymercuration reaction, uses highly toxic mercury reagents, and has large pollution and large Potential safety hazards, mercury residues are difficult to remove, and it is difficult to realize industrialization; [0006] (b) epoxy oxidation method [0007] [0008] This method (Chem.Pharm.Bull.21(2), 457...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00
CPCC07J9/00
Inventor 张先南张大玮王玉尧陈璋李泳司玉贵
Owner 江西天新药业股份有限公司
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