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High-efficiency synthesis method of artemisinin

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

Active Publication Date: 2015-05-20
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 synthesis method of artemisinin

Examples

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Effect test

Embodiment 1

[0045] (1) Synthesis of dihydroartemisinic acid 2

[0046] 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%).

[0047] (2) Synthesis of dihydroartemisinic acid 3 peroxide

[0048] 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

[0052] (1) Synthesis of dihydroartemisinic acid 2

[0053] 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%).

[0054] (2) Synthesis of dihydroartemisinic acid 3 peroxide

[0055] 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

[0059] (1) Synthesis of dihydroartemisinic acid 2

[0060] 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%).

[0061] (2) Synthesis of dihydroartemisinic acid 3 peroxide

[0062] 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 synthesis method of artemisinin. The method comprises the following steps of: enabling dihydroartemisinic acid to be subjected to carboxyl protection so as to obtain a dihydroartemisinic acid derivative, and oxidizing the dihydroartemisinic acid derivative into a corresponding peroxidized dihydroartemisinic acid derivative by peroxide in the presence of a catalyst, thus obtaining a target product, namely artemisinin, in a high-yield manner under the catalysis of acid and the action of oxygen gas. Compared with the prior art, the method has the following advantages that applied reagents are cheap and easily available, a synthesis route is short, the reaction selectivity is high, the preparation process is environment-friendly, the operation and after-treatment are simple, and the overall yield is high, thereby being applicable to 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 method for preparing an antimalarial drug artemisinin. 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 of its derivatives,...

Claims

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Application Information

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Patent Type & Authority Patents(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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