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Asymmetric syntheses method of (-)-sodium danshensu and application thereof

A synthetic method, the technology of Danshensu Sodium, which is applied in the field of medicine and chemical industry, can solve the problems of long route and expensive chemical reagents, and achieve the effect of high purity, simple operation and conflict resolution

Active Publication Date: 2015-07-01
HEBEI YILING MEDICINE INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the routes used are long and some of the chemicals are expensive

Method used

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  • Asymmetric syntheses method of (-)-sodium danshensu and application thereof
  • Asymmetric syntheses method of (-)-sodium danshensu and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0057] Step A: Synthesis of S-3-(3,4-Diacetylphenyl)-2-aminopropionic acid hydrochloride

[0058] Add 40 grams of levodopa and 400 ml of acetic acid into a 1000 ml three-necked flask, stir at room temperature, the solution is in a swirling state, pass through dry hydrogen chloride gas, and stir for 1 hour. Raise the reaction temperature to 50°C, then add 30ml of acetyl chloride, continue to pass through dry hydrochloric acid gas until the solution becomes clear, then terminate the reaction, and slowly cool the reaction system to room temperature, a large amount of white solids are precipitated, pumping Filter, wash with ice water, and dry to obtain S-3-(3,4 diacetylphenyl)-2-aminopropionic acid hydrochloride as a white solid. The yield is about 90%.

[0059] Step B: Synthesis of S-3-(3,4 diacetylphenyl)-2-hydroxypropionic acid

[0060] Add 16.2 grams of S-3-(3,4 diacetylphenyl)-2-aminopropionic acid hydrochloride obtained in step A to a 1000ml three-neck flask, add a mixed ...

Embodiment 2

[0066] Step A: Synthesis of S-3-(3,4-Diacetylphenyl)-2-aminopropionic acid hydrochloride

[0067] Add 50 grams of levodopa and 400 ml of acetic acid into a 1000 ml three-neck flask, stir at room temperature, the solution is in a swirling state, pass through dry hydrogen chloride gas, and stir for 1 hour. Raise the reaction temperature to 50°C, then add 50ml of acetyl chloride, continue to pass through dry hydrochloric acid gas until the solution becomes clear, then terminate the reaction, and slowly cool the reaction system to room temperature, a large amount of white solids are precipitated, pumping Filter, wash with ice water, and dry to obtain 20 g of white solid.

[0068] Step B: Synthesis of S-3-(3,4 diacetylphenyl)-2-hydroxypropionic acid

[0069] Add 20 grams of S-3-(3,4 diacetylphenyl)-2-aminopropionic acid hydrochloride obtained in step A to a 1000ml three-necked flask, add a mixed solution of 100ml glacial acetic acid and 375ml water, and Stir to dissolve, and gra...

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Abstract

The invention discloses an asymmetric syntheses method of (-)-sodium danshensu and an application thereof, which belongs to the medicine chemical field. The method comprises the following steps: A)taking levodopa shown in a formula I as a raw material, and performing a hydroxyl acetylation to obtain S-3-(3,4-acetylphenyl)-2-alanine hydrochloride; B)performing a diazotization reaction on S-3-(3,4-acetylphenyl)-2-alanine hydrochloride obtained in the step A) to obtain S-3-(3,4-acetylphenyl)-2-hydracrylicacid in a formula III; C)performing hydrolysis on the S-3-(3,4-acetylphenyl)-2-hydracrylicacid in the step B to obtain S-3-(3,4-dihydroxy phenyl)-2-hydracrylicacid shown in a formula IV; and D)dropping a sodium bicarbonate saturated solution in the S-3-(3,4-dihydroxy phenyl)-2-hydracrylicacid to react to obtain sodium salt (-)-sodium danshensu shown in a formula V. The method has the advantages of easily available raw material and simple operation, and the (-)-sodium danshensu has good effect for treating myocardial ischemia and myocardial infarction.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a method for synthesizing a substance and its application. Background technique [0002] Natural tanshinol is the main water-soluble component of Salvia miltiorrhiza Bge., a plant of Labiatae, and its chemical name is D-(+)-β-(3,4-dihydroxyphenyl) lactic acid. In the treatment of cardiovascular diseases, it shows a unique curative effect. Studies in recent years have also shown a wider range of pharmacological effects. Development prospects are good. At present, Danshensu mainly comes from plants, and its content in Danshen is only 5 / 1000. The source of the original plant is very limited. In addition, the extraction and separation steps are cumbersome and difficult to purify, which limits the large-scale application of Danshensu. Therefore, organic Chemists have been exploring synthetic methods to solve these problems. [0003] At present, the synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/52C07C51/41A61K31/192A61P9/10
CPCC07C51/377C07C51/412C07C67/29C07C227/18C07C59/52C07C69/18C07C229/34
Inventor 闫建辉姚子俭陈媛杨丽娜王翠翠孟二辉郝梦安杨青瑞卢会刚安堃粱辰唐思文张彦芬朱慧明王海荣王宏涛
Owner HEBEI YILING MEDICINE INST
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