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Synthesis method of tanshinol

A synthesis method and technology of danshensu are applied in chemical instruments and methods, preparation of oxygen-containing compounds, preparation of organic compounds, etc., which can solve problems such as limiting the industrial production of danshensu, and achieve the effects of easy availability of raw materials and simple operation.

Active Publication Date: 2014-11-26
北京华素制药股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These all limit the industrialized production of Danshensu

Method used

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  • Synthesis method of tanshinol
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  • Synthesis method of tanshinol

Examples

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Embodiment 1

[0055] Synthesis of D-(+)-2-amino-3-(4-benzylphenyl)propionic acid (D1)

[0056] Into a 5000 mL three-neck flask, add 144.9 g of D-tyrosine, add 800 mL of 2N sodium hydroxide solution, stir evenly, raise the temperature to 60°C and stir for 1 hour. Stop heating, lower to room temperature, add 2400mL methanol, add 95mL benzyl bromide, react for 3 hours. Adjust to acidity with hydrochloric acid, filter, wash the filter cake with 2000 mL of water, wash with 400 mL of ethanol, and dry to obtain 142 g of D1. Yield: 69.1%.

[0057] Synthesis of D-(+)-2-amino-3-(4-benzylphenyl)propionic acid (D1)

[0058] Into a 5000 mL three-neck flask, add 144.9 g of D-tyrosine, add 800 mL of 2N sodium hydroxide solution, stir evenly, raise the temperature to 60°C and stir for 1 hour. Stop heating, lower to room temperature, add 2400mL methanol, add 100mL benzyl bromide, and react for 3 hours. Adjust to acidity with hydrochloric acid, filter, wash the filter cake with 2000 mL of water, wash wit...

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Abstract

The invention discloses a synthesis method of tanshinol, which mainly comprises the following steps of: 1) taking D-tyrosine as starting material, and carrying out diazo-reaction between the D-tyrosine and nitrite; and 2) using the diazotized product to act on hypervalent iodine compound to obtain the tanshinol. The synthetic route is shown by a figure; and according to the synthesis method, the raw material is low in price and can be easily obtained, and the operation is simple and convenient, so that the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of danshensu. 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. Pharmacological research results show that Danshensu has multiple functions such as myocardial protection, antithrombosis, nerve cell protection, prevention and treatment of liver fibrosis and anti-tumor, and is an active ingredient in compound Danshen dripping pills and Danshen injection. It has high clinical application value. At present, Danshensu is mainly derived 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. Organic chemists have been exploring synthetic methods to solve these problems. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/52C07C27/02
CPCY02P20/55
Inventor 米春来董剑英魏淑冬边玢翟海燕姚文静龙永鹏周辛波郑志兵
Owner 北京华素制药股份有限公司