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Synthetic method for salvianolic acid A

A synthesis method and technology of salvianolic acid, applied in the field of synthesis of salvianolic acid A, can solve problems such as obtaining salvianolic acid A and difficult natural products

Inactive Publication Date: 2015-11-25
TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the problem that it is difficult to obtain salvianolic acid A from natural products in the prior art, the invention provides a method for synthesizing salvianolic acid A

Method used

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  • Synthetic method for salvianolic acid A
  • Synthetic method for salvianolic acid A
  • Synthetic method for salvianolic acid A

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of embodiment 1 compound 2

[0028]

[0029] Dissolve 34.0 g (0.21 mol) of 2,3-dimethoxybenzaldehyde (1) in 120 ml of methanol and keep stirring. Weigh 4.7g (0.124mol) of sodium borohydride and carefully add to the reaction solution in batches. Then, it was stirred at room temperature for 1 h, and analyzed by TLC, the reaction was complete. The reaction was stopped, and the solvent methanol was removed by rotary evaporation. The residue was dissolved in dichloromethane, washed with water, washed with saturated brine, and dried over anhydrous magnesium sulfate. Filter and remove the solvent to obtain a light gray viscous liquid, which becomes a solid after standing and weighs 34.0 g (yield 99%). spare.

Embodiment 2

[0030] The synthesis of embodiment 2 compound 3

[0031]

[0032]Weigh 16.8g (0.1mol) of 2,3-dimethoxybenzyl alcohol (2) and dissolve it in 450ml of dichloromethane to completely dissolve it, and cool down to 0°C in an ice bath. 17.6g (5.64ml) of liquid bromine was dissolved in 50ml of dichloromethane and placed in a constant pressure dropping funnel. During the dropwise addition, the temperature was kept below 5°C. After about 0.5 hours, the dropwise addition was completed, and the ice bath was removed, and the temperature rose to room temperature. The reaction was monitored by TLC over time. After about 2 hours, the reaction was completed. Immediately, 100ml of 1M sodium bicarbonate solution was added to the solution, extracted, washed with water, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation to obtain a yellow viscous substance, which was recrystallized from methanol to obtain a yellow crystal, wh...

Embodiment 3

[0033] The synthesis of embodiment 3 compound 4

[0034]

[0035] Dissolve 22g of compound 3 in 500ml of toluene, add 18.6g of triphenylphosphine, and stir vigorously. And began to heat up to reflux, after stirring for about 10 minutes, the solution began to become cloudy, and a white solid was produced. After reflux for 4 hours, it was cooled to room temperature, and a large amount of white precipitate was formed, which was filtered and dried in vacuo. 38.5 g of white solid were obtained, yield 95%. Mp169°C. 1H-NMR (400MHz, CDCl3): 3.75(s, 3H), 3.79(s, 3H), 5.16(d, 2H, J=14Hz), 6.75(d, 1H, J=8.8Hz), 7.05(d, 1H, J=8.8Hz), 7.58-7.82 (m, 15H).

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Abstract

The invention provides a synthetic method for salvianolic acid A. The synthetic method is characterized by comprising a step of subjecting a salvianolic acid A synthetic precursor (10) to demethylation so as to prepare salvianolic acid A. A synthetic route is described in the specification. The prepared salvianolic acid A has a purity of 90 to 94%; and the purity of the prepared salvianolic acid A can be increased to 97% after preparative HPLC purification.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a synthesis method of salvianolic acid A. Background technique [0002] The traditional Chinese medicine Salvia miltiorrhiza is the dried root of Salvia miltiorrhiza Bunge, a plant of the genus Salvia in the family Labiatae. Bitter in taste and slightly cold in nature, Salvia miltiorrhiza is one of the most commonly used medicinal materials. It is used to treat cardiovascular and cerebrovascular diseases such as angina pectoris, high blood pressure, coronary heart disease and stroke. The effect of muscle, is the commonly used herbal flavor of traditional Chinese medicine for promoting blood circulation and eliminating addiction. Clinical studies have also confirmed that Salvia miltiorrhiza contains a variety of chemical components and has a wide range of biological activities. Its traditional pharmacology is mainly to expand blood vessels, activate blood circulation and remove...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/297
Inventor 陈卫强周红刚李金楠孙波冯金磊
Owner TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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