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Industrial stereospecific synthesis of beta-artemether by using artemisinin as raw material

A technology of artemether and artemisinin, which is applied in the direction of organic compound/hydride/coordination complex catalyst, organic chemistry, drug combination, etc., can solve the problems of unfriendly environment, uneconomical, time-consuming, etc., and achieve reduction The use of organic solvents, the reduction of pollutants, and the effect of reducing intermediate processes

Inactive Publication Date: 2010-10-13
GUANGZHOU SWELLXIN SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The artemether preparation method described above has disadvantages such as low stereoselectivity, uneconomical, time-consuming, and unfriendly to the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Weigh 5.00 kg of artemisinin into a stainless steel reactor, add 50.00 L of dichloromethane, stir and dissolve at room temperature. The freezing device controls the temperature in the stainless steel reactor to 0°C, first add 500mL of tert-butoxyaluminum, and then dropwise add 3.00L of sodium borohydride aqueous solution containing 0.1-0.5% sodium hydroxide, containing 0.95kg of sodium borohydride, drop within 30 minutes Finished adding. Control the temperature between -10 and 10°C, and react for 1.5 hours until the raw material point of artemisinin disappears. Stand to separate layers, suck out the upper aqueous phase, control the temperature in the three-necked flask below 0°C, then add 20.00 L of methanol and 0.5 kg of sodium bisulfate, and then react at room temperature for 2.0 h. Cool, add 500 mL of water, and extract 3 times with 300 mL of dichloromethane. The organic phases were combined, dried by adding 5.0 kg of anhydrous sodium sulfate, and concentrated in a...

Embodiment 2

[0015] Weigh 5 g of artemisinin into a three-necked bottle, add 20 mL of dichloromethane, and stir at room temperature to dissolve. The freezing device controls the temperature in the three-necked bottle to 0°C, and first adds 0.5 mL of tert-butoxyaluminum. Then add dropwise 5.00 mL of sodium borohydride aqueous solution containing 0.1-0.5% sodium hydroxide, containing 1.0 g of sodium borohydride, and the dropwise addition is completed within 10 minutes. The reaction temperature was controlled at 0°C, and the reaction was carried out for 1 hour until the raw material sites of artemisinin disappeared. Stand to separate layers, suck out the upper aqueous phase, control the temperature in the three-neck flask to 0°C, add 20 mL of methanol and 5.0 g of aluminum perchlorate, and react at room temperature for 2 h. The post-treatment method was the same as above, and 0.54 g of pure α-artemether and 4.38 g of β-artemether were obtained with a total yield of 93.2%. The ratio of α-art...

Embodiment 3

[0017] Weigh 5 g of artemisinin into a three-necked bottle, add 20 mL of dichloromethane, and stir at room temperature to dissolve. The freezing device controls the temperature in the three-necked bottle to 0°C, and first adds 0.5 mL of tert-butoxyaluminum. Then add dropwise 5.00 mL of sodium borohydride aqueous solution containing 0.1-0.5% sodium hydroxide, containing 1.0 g of sodium borohydride, and the dropwise addition is completed within 10 minutes. The reaction temperature was controlled at 0°C, and the reaction was carried out for 1 hour until the raw material sites of artemisinin disappeared. Stand to separate layers, suck out the upper aqueous phase, control the temperature in the three-necked flask to 0°C, then add 20 mL of methanol and 5.0 g of nickel perchlorate, and then react at room temperature for 2 h. The post-treatment method was the same as above, and 0.74 g of pure α-artemether and 4.17 g of β-artemether were obtained with a total yield of 93.0%. The rati...

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Abstract

The invention discloses stereospecific synthesis of beta-artemether by using artemisinin as a raw material through a one-pot method, which comprises the following steps of: in a system of alkaline solution of dichloromethane, taking sodium borohydride as a reducing agent and aluminium tert-butoxide as a catalyst, and reducing to obtain dihydroartemisinin; and separating out a water phase, adding methanol, sodium acid sulfate, aluminum perchlorate nonahydrate, nickelousperchlorate and the like serving as catalysts for methyl etherification, and reacting at room temperature for 2 hours to obtain the beta-artemether, wherein the maximum yield rate of the beta-artemether is 85 percent and the maximum total yield rate of artemether is 93.5 percent. The method has the characteristics of low cost, high yield, short time and simple and safe operation, and is completely suitable for industrial production.

Description

technical field [0001] The invention relates to an antimalarial drug artemisinin derivative artemether, in particular to a semi-synthetic method for artemether. Background technique [0002] According to the latest report of the World Health Organization, malaria is an infectious disease with a clear upward trend in the world except AIDS. It is a communicable disease in tropical and subtropical regions, endangering the health of two billion people; Many people were infected and about 3 million people (mostly children) died, especially in Africa has become the number one killer. For this reason, in 2004, Nature magazine published a number of reviews and prospects, discussing how to prevent and treat malaria and related research progress (Nature, 2004, 430:7002). [0003] Artemisinin is a new effective antimalarial compound that was isolated from Artemisia annua L. on the basis of Chinese scholars' research on "Elbow Reserve Emergency Prescription" written by Han Dynasty phar...

Claims

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Application Information

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IPC IPC(8): C07D493/18A61P33/06B01J31/14B01J27/053B01J27/125B01J27/128
Inventor 彭学东王正濂赵金召
Owner GUANGZHOU SWELLXIN SCI & TECH
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