Synthetic method for flavonoid glycoside drug intermediate propiolic acid

A synthesis method and technology of propiolic acid, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylate, etc., can solve the problems of increased risk factor, large environmental pollution, high processing cost, etc., and achieve an increase in reaction yield , avoid pollution, improve the effect of reaction yield

Inactive Publication Date: 2018-07-03
CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This synthetic method needs to use the sulfuric acid solution of chromic anhydride, because chromic anhydride pollutes the environment bigger, and the follow-up pollution treatment cost is higher, and sulfuric acid solution can cause the risk coefficient of reaction process to increase as reactant, and the whole synthetic process technology is more complicated, therefore It is necessary to propose a new synthetic method

Method used

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  • Synthetic method for flavonoid glycoside drug intermediate propiolic acid
  • Synthetic method for flavonoid glycoside drug intermediate propiolic acid
  • Synthetic method for flavonoid glycoside drug intermediate propiolic acid

Examples

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Comparison scheme
Effect test

Embodiment 1

[0018] The synthetic method of flavone glycoside drug intermediate propiolic acid comprises the steps:

[0019] A: Add 2mol 3-aminopropyne and 1.5L of sodium nitrate solution with a mass fraction of 10% in the reaction vessel, control the stirring speed at 210rpm, control the solution temperature to 25°C, react for 60min, and add 800ml of 20% sodium nitrate solution with a mass fraction of Base tert-butyl ether solution, raise the temperature of the solution to 40°C, and react for 1h;

[0020] B: Add 2 mol of antimony pentachloride powder, 4 mol mass fraction of 40% diglycol diacetate solution, increase the solution temperature to 50 ° C, react for 30 min, extract 3 times with ethyl tert-butyl ether solution, static Set aside for 2h, the solution was separated into layers, and the oil layer was separated, washed 5 times in a potassium chloride solution with a mass fraction of 15%, and washed 6 times in a 3-methyl-2-pentanone solution with a mass fraction of 50%. Washed 8 time...

Embodiment 2

[0022] The synthetic method of flavone glycoside drug intermediate propiolic acid comprises the steps:

[0023] A: Add 2mol 3-aminopropyne and 1.5L of sodium nitrate solution with a mass fraction of 13% in the reaction vessel, control the stirring speed at 220rpm, control the solution temperature to 27°C, react for 70min, and add 800ml of 25% sodium nitrate solution with a mass fraction of Base tert-butyl ether solution, raise the temperature of the solution to 43°C, and react for 1.5h;

[0024] B: Add 2.5 mol of antimony pentachloride powder, 4.5 mol of diglycol diacetate solution with a mass fraction of 43%, raise the temperature of the solution to 52°C, react for 40 minutes, and extract 4 times with ethyl tert-butyl ether solution , standing for 2.5h, the solution was separated, and the oil layer was separated, washed 6 times in a potassium chloride solution with a mass fraction of 18%, and washed 7 times in a 3-methyl-2-pentanone solution with a mass fraction of 54%. , wa...

Embodiment 3

[0026] The synthetic method of flavone glycoside drug intermediate propiolic acid comprises the steps:

[0027] A: Add 2mol 3-aminopropyne and 1.5L of sodium nitrate solution with a mass fraction of 16% in the reaction vessel, control the stirring speed at 230rpm, control the solution temperature to 30°C, react for 80min, and add 800ml of 27% sodium nitrate solution with a mass fraction of Base tert-butyl ether solution, raise the temperature of the solution to 45°C, and react for 2h;

[0028] B: Add 3mol antimony pentachloride powder, 5mol mass fraction of 46% diglycol diacetate solution, increase the solution temperature to 56°C, react for 50min, extract 5 times with ethyl tert-butyl ether solution, static Set aside for 2-3h, the solution was separated, and the oil layer was separated, washed 7 times in a potassium chloride solution with a mass fraction of 22%, and washed 8 times in a 3-methyl-2-pentanone solution with a mass fraction of 55%. Washing 10 times in dipropylene...

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Abstract

The invention discloses a synthetic method for the flavonoid glycoside drug intermediate propiolic acid. The synthetic method comprises the following steps: adding 3-aminopropyne and a sodium nitratesolution into a reaction vessel, controlling a stirring speed, controlling the temperature of the obtained solution, carrying out a reaction, adding an ethyl tert-butyl ether solution, raising solution temperature and carrying out a reaction; and adding antimony pentachloride powder and a diglycol diacetate solution, raising solution temperature, carrying out a reaction, then carrying out extraction with the ethyl t-butyl ether solution a plurality of times, carrying out standing for laying of the obtained solution so as to separate an oil layer, washing the oil layer with a potassium chloridesolution a plurality of times, washing the oil layer with a 3-methyl-2-pentanone solution a plurality of times, then washing the oil layer with a dipropylene glycol solution a plurality of times, carrying out recrystallization in a 1,3-dimethylcyclohexane solution and then carrying out dehydration with a dehydrating agent so as to obtain the finished propiolic acid.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, belonging to the field of organic synthesis, in particular to a synthesis method of a flavonoid glycoside drug intermediate propiolic acid. Background technique [0002] Propiolic acid is mainly used in the synthesis of flavonoid glycosides, which are tea polyphenols and belong to flavonoids. Flavonoids are a class of compounds that exist in nature and have the structure of 2-phenylchromanone. There is a ketone carbonyl group in their molecules, and the oxygen atom at the first position is basic and can form a salt with a strong acid. Most of its hydroxyl derivatives are yellow, so they are also called flavonoids or flavonoids. Generally, it has the functions of lowering blood pressure, antibacterial and regulating blood osmotic pressure, and it has also been found to have the function of inhibiting tumor cells and protecting against ultraviolet rays. Most of the existing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/29C07C57/20
CPCC07C51/29C07C57/20
Inventor 关艮安
Owner CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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