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Preparation method of beta-artemether

A technology for artemether and artemisinin, which is applied in the field of preparing beta-artemether, can solve the problems of low artemether yield and low product purity, and achieves a high yield and purity, environment-friendly and mild conditions. Effect

Active Publication Date: 2012-10-17
湖南莱崔尔生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because isomers are easily produced in the etherification reaction, the current industrial production of artemether generally has the defects of low yield and low product purity.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] This embodiment includes the following steps:

[0026] (1) Under the action of a reducing agent, artemisinin reacts to form dihydroartemisinin:

[0027] In a clean and dry 1000mL reaction bottle, add 80g of artemisinin and 400mL of anhydrous methanol, dissolve at room temperature; cool down to 5°C, add 16g of sodium borohydride, during the addition, control the reaction temperature at 5±0.3°C, reaction 2 hour; filter, the resulting filtrate is concentrated to 42mL at a vacuum degree of -0.06MPa and a temperature of 50°C, add 150mL of pure water, crystallize for 2 hours, filter, and wash the filter cake with pure water to neutrality. Drying at 60°C to constant weight yielded 78g of dihydroartemisinin with a purity of 98.6wt%;

[0028] (2) Dihydroartemisinin reacts with p-toluenesulfonic acid to generate β-artemether:

[0029] In a clean and dry 1000mL reaction bottle, first add 800mL of anhydrous methanol, then add 2.4g of p-toluenesulfonic acid, then add 78g of dihydr...

Embodiment 2

[0032] This embodiment includes the following steps:

[0033] (1) Under the action of reducing agent, artemisinin reacts to form dihydroartemisinin:

[0034] In a clean and dry 1000mL reaction bottle, add 80g of artemisinin and 500mL of absolute ethanol, dissolve at room temperature; cool down to 5°C, add 16g of potassium borohydride, during the addition, control the reaction temperature at 5±0.3°C, reaction 2 hour, the reaction is complete; filter, and concentrate the obtained filtrate to 52mL at a vacuum degree of -0.06MPa and a temperature of 60°C, add 200mL of pure water, crystallize for 2 hours, filter, wash the filter cake with pure water until neutral, and obtain The filter cake was dried at 60°C to constant weight to obtain 76g of dihydroartemisinin with a purity of 98.0wt%;

[0035] (2) Dihydroartemisinin reacts with p-toluenesulfonic acid to generate β-artemether:

[0036] In a clean and dry 1000mL reaction bottle, first add 800mL of absolute ethanol, then add 2.3g...

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PUM

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Abstract

The invention provides a preparation method of beta-artemether. The method comprises the following steps: (1) artemisnin reacts to generate dihydroartemisinin in the action of a reducing agent; (2) the dihydroartemisinin reacts with p-toluenesulfonic acid to generate beta-artemether; and (3) refining: methanol, ethanol, ethylene glycol or isopropyl alcohol which is equivalent to 2 to 4 times the weight of the artemether crude product is added into the artemether crude product, the mixture is heated to a temperature of between 35 and 45 DEG C and dissolved, cooled to room temperature in a stirring condition, cooled to a temperature of between 0 and 5 DEG C, and crystallized for 3 to 5 hours, the mixture is filtered, the prepared filter cake is cleaned with frozen methanol, ethanol, ethylene glycol or isopropyl alcohol the weight of which is equivalent to 0.5 to 1 time that of the filter cake at a temperature of between 0 and 5 DEG C, and the filter cake is baked at a temperature of between 35 and 45 DEG C to a constant weight. The preparation method of the beta-artemether has mild condition and environmental friendliness and is suitable for industrial production; and the product yield is over 90 percent, and the purity is 99.2 percent.

Description

technical field [0001] The invention relates to a method for preparing β-artemether. Background technique [0002] Malaria is a vector-borne disease caused by Plasmodium infection through mosquito bites. Malaria is widely prevalent all over the world. According to the statistics of the World Health Organization, 92 countries and regions are still highly and moderately endemic, with 150 million cases of malaria each year and more than 2 million deaths from malaria. Therefore, malaria remains one of the greatest health killers for humans. [0003] Artemisinin is an antimalarial drug with specific effects on drug-resistant malaria, which was extracted and isolated from the traditional Chinese medicine Artemisia annua by Chinese scientists in 1972. Due to the low solubility of artemisinin in water, resulting in low bioavailability and high reactivation rate, medicinal chemists try to synthesize many artemisinin series by modifying the side chain of artemisinin and modifying th...

Claims

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Application Information

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IPC IPC(8): C07D493/20
Inventor 刘志强
Owner 湖南莱崔尔生物科技有限公司
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