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Synthesis method of 25-hydroxycholesteryl acetate-7-p-toluenesulfonylhydrazone

A technology of p-toluenesulfonyl hydrazone and hydroxycholesterol, applied in the field of medicine and chemical industry, can solve the problems of long reaction time, low yield, corrosion of production equipment, etc., and achieve the effects of simple operation, high yield and less three wastes

Active Publication Date: 2015-12-09
ZHEJIANG GARDEN BIOCHEM HIGH TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to solve the problems of long reaction time, low yield and serious corrosion of production equipment in the synthetic method of 25-hydroxycholesterol acetate-7-p-toluenesulfonylhydrazone in the prior art, and provide a kind of simple and convenient operation and Efficient, and the synthetic method of 25-hydroxycholesterol acetate-7-p-toluenesulfonylhydrazone without using organic solvents, environmental protection and energy saving

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] At room temperature, add 5.0g (10mmol) of 25-hydroxy-7-ketocholesterol diacetate and 1.86g (10mmol) of p-toluenesulfonyl hydrazide into the ball milling jar, and react for 0.2 hours after ball milling. Recrystallized from water and ethanol to obtain 6.42 g of white solid 25-hydroxycholesterol diacetate-7-p-toluenesulfonylhydrazone, with a yield of 96%.

[0028] After testing, the specific characteristics of the product are as follows:

[0029] Melting point: 146~148℃, 1 HNMR (400MHz, CDCl 3 )δ=7.84(d, J =8.0Hz,2H),7.30(d, J =8.0Hz,2H),5.95(s,1H),4.59-4.64(m,1H),2.43(m,3H),2.26-2.20(m,2H),2.05(s,3H),2.00-2.03( m,1H),1.98(s,3H),1.48-1.92(m,8H),1.44(m,6H),1.15-1.42(m,8H),1.11(s,3H),1.02-1.07(m, 5H),0.92-0.93(m,4H),0.66(s,3H).MS(ESI): m / z ( % )=669.4(M + +1).

Embodiment 2

[0031] The molar ratio of 25-hydroxy-7-ketocholesterol diacetate (5.0g (10mmol)) to p-toluenesulfonyl hydrazide is 1:2, and other operations are the same as in Example 1 to obtain 25-hydroxycholesterol diacetate-7 - p-toluenesulfonylhydrazone 6.36g, yield 95%.

Embodiment 3

[0033] The molar ratio of 25-hydroxy-7-ketocholesterol acetate (5.0g (10mmol)) to p-toluenesulfonyl hydrazide is 1:5, and other operations are the same as in Example 1 to obtain 25-hydroxycholesterol acetate-7-p- Tosylhydrazone 6.15g, yield 92%.

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Abstract

The invention relates to the technical field of medicine chemical engineering and particularly relates to a synthesis method of 25-hydroxycholesteryl acetate-7-p- toluenesulfonylhydrazone. The synthesis method includes following steps: (1) performing a reaction between 25-hydroxy-7-ketocholesteryl acetate and p-toluenesulfonylhydrazide under a mechanical grinding condition; and (2) performing recrystallization to a reaction product in the step (1) to obtain the 25-hydroxycholesteryl acetate-7-p-toluenesulfonylhydrazone. The method is free of an acidic catalyst, is greatly reduced in usage of organic solvent, is simple in operation, is high in yield, is less in waste gas, waste water and solid waste and is simple in post-treatment. The product is easy to separate and purify.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a method for synthesizing 25-hydroxycholesterol acetate-7-p-toluenesulfonyl hydrazone. Background technique [0002] 25-hydroxycholesterol acetate-7-p-toluenesulfonylhydrazone is the raw material for the synthesis of 25-hydroxy-7-dehydrocholesterol, and 25-hydroxyvitamin D can be synthesized from 25-hydroxy-7-dehydrocholesterol after ultraviolet light irradiation 3 . 25-Hydroxyvitamin D 3 Also known as calcifediol, vitamin D 3 The active metabolite of the liver in the human body has strong physiological activity and can be used in medicine and feed, and can also be used as a raw material to prepare calcitriol 1α, 25-dihydroxyvitamin D 3 . [0003] In the prior art, 25-hydroxycholesterol acetate-7-p-toluenesulfonylhydrazone is generally prepared from 7-keto-25-acetoxycholesterol acetate as a raw material, which is reacted with p-toluenesulfonylhydrazide ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
Inventor 王子强金灿苏为科刘建刚钱国平方楚王庆华
Owner ZHEJIANG GARDEN BIOCHEM HIGH TECH
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