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High-efficiency preparation method of anti-malarial medicine artemisinin

An artemisinin and anti-malarial technology, applied in the field of biomedicine, can solve the problems of unfavorable environmental protection and industrial production, difficulty in realizing industrial production, long artemisinin synthesis route, etc., and achieve easy large-scale production, cheap reagents, and high yield high effect

Active Publication Date: 2013-07-10
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the selectivity of the product obtained is poor, and there are many by-products, resulting in a low total yield of artemisinin (<20%), and it is difficult to realize industrial production
[0006] In summary, the existing methods for the preparation of artemisinin have long synthetic routes, cumbersome operations, poor atom economy, and low overall yield, which are not conducive to environmental protection and industrial production.

Method used

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  • High-efficiency preparation method of anti-malarial medicine artemisinin

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Embodiment 1

[0044] (1) Synthesis of dihydroartemisinic acid 2

[0045] Artemisinic acid (100 g, 427 mmol) and 10% Pd / C (4.3 mmol) were added to 1000 mL of methanol, and reacted at -50 °C in a hydrogen atmosphere (1 bar) for 24 hours. The reaction mixture was filtered through celite, and the organic solvent was removed by rotary evaporation to obtain a white solid (99 g, 98%).

[0046] (2) Synthesis of dihydroartemisinic acid 3 peroxide

[0047] Dihydroartemisinic acid (99 g, 420 mmol), potassium dichromate (4.2 mmol), potassium carbonate (4.2 mmol) were added to 1000 mL of acetonitrile. At -78°C, slowly add 30% hydrogen peroxide (420 mmol) dropwise to the system, and react overnight. The organic solvent was removed by rotary evaporation, the residual phase was extracted with ethyl acetate (500mL×3), the combined organic phases were dried over anhydrous sodium sulfate, filtered by suction, the solvent was removed by rotary evaporation, and the product was directly put into the next react...

Embodiment 2

[0051] (1) Synthesis of dihydroartemisinic acid 2

[0052] Artemisinic acid (100 g, 427 mmol) and 10% Pd / C (427 mmol) were added to 1000 mL of isopropanol, and reacted at 25 °C in a hydrogen atmosphere (1 bar) for 12 hours. The reaction mixture was filtered through celite, and the organic solvent was removed by rotary evaporation to obtain a white solid (100 g, 99%).

[0053] (2) Synthesis of dihydroartemisinic acid 3 peroxide

[0054] Dihydroartemisinic acid (100 g, 424 mmol), sodium perchlorate (424 mmol), and pyridine (424 mmol) were added to 1000 mL of acetone. At -78°C, 30% hydrogen peroxide (4.2 mol) was slowly added dropwise to the reaction mixture and reacted overnight. The organic solvent was removed by rotary evaporation, the residual phase was extracted with ethyl acetate (500mL×3), the combined organic phases were dried over anhydrous sodium sulfate, filtered by suction, the solvent was removed by rotary evaporation, and the product was directly put into the next...

Embodiment 3

[0058] (1) Synthesis of dihydroartemisinic acid 2

[0059] Artemisinic acid (100g, 427mmol), Al 2 o 3 / Rh (4.3mmol) was added into 1000mL of methanol, and reacted at -50°C in a hydrogen atmosphere (1 bar) for 24 hours. The reaction mixture was filtered through celite, and the organic solvent was removed by rotary evaporation to obtain a white solid (99 g, 98%).

[0060] (2) Synthesis of dihydroartemisinic acid 3 peroxide

[0061] Dihydroartemisinic acid (99 g, 420 mmol), sodium hypochlorite (4.2 mmol), sodium hydroxide (4.2 mmol) were added to 1000 mL of acetonitrile. At -40°C, 30% hydrogen peroxide (420 mmol) was slowly added dropwise to the system, and reacted overnight. The organic solvent was removed by rotary evaporation, the residual phase was extracted with ethyl acetate (500mL×3), the combined organic phases were dried over anhydrous sodium sulfate, filtered by suction, the solvent was removed by rotary evaporation, and the product was directly put into the next re...

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Abstract

The invention discloses a high-efficiency preparation method of anti-malarial medicine artemisinin. The method comprises the following steps of: preparing dihydroartemisinic acid from artemisinin under the action of reducing agent sodium borohydride / nickel chloride or hydrogen / metal catalyst; oxidizing the dihydroartemisinic acid by peroxide in the existence of the catalyst to obtain oxidized dihydroartemisinic acid; and preparing the target product artemisinin with high yield under catalysis of acid and the action of oxygen. Compared with the prior art, the method has the advantages of low price and easy availability of reagents, short synthetic route, high reaction selectivity, environmentally-friendly preparation process, simplicity in operation and post-treatment and high total yield, and is suitable for industrial production.

Description

[0001] This application is a divisional application with the application number 201210181561.7, the filing date is 2012.6.5, and the invention title is "A Method for Preparing Artemisinin from Artemisinic Acid". technical field [0002] The invention relates to the field of biomedicine, in particular to a high-efficiency preparation method of artemisinin, an antimalarial drug. Background technique [0003] Artemisinin, a sesquiterpene lactone antimalarial drug with peroxy groups extracted from the traditional Chinese medicine Artemisia annua, is the first internationally recognized natural medicine discovered in China. The antimalarial mechanism of artemisinin is different from other antimalarial drugs. Its main function is to interfere with the membrane-mitochondrion function of Plasmodium, rather than interfere with folic acid metabolism, resulting in the complete collapse of parasite structure. In addition, artemisinin can be used as raw material to synthesize a variety o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20
Inventor 张万斌刘德龙袁乾家
Owner SHANGHAI JIAO TONG UNIV
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