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Preparation method of artemether

A technique for artemether and methanol, which is applied in the field of medicinal chemical synthesis, can solve the problems of complicated operation, low yield and low β-artemether content, and achieves the effects of reduced production cost, short technological process and simple operation.

Inactive Publication Date: 2018-03-13
TIANJIN PACIFIC PHARMA
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  • Abstract
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Problems solved by technology

[0006] The early methods of synthesizing β-artemether include: etherification reaction of dihydroartemisinin (also known as reduced artemisinin) and methanol under the catalysis of boron trifluoride ether at room temperature, and column chromatography after the reaction Separation is carried out to obtain the crude product of β-artemether, and the yield is relatively low (see "Synthesis of Artemisinin Derivatives", Li Ying et al., Science Bulletin, 1979, 24 (14), 667-9), and the operation is complicated, Not suitable for industrial production
[0007] Patent CN200910038509.4 "Using artemisinin as raw material for industrialized directional synthesis of β-artemether" provides a dichloromethane alkaline aqueous solution system, using sodium borohydride as a reducing agent and a tert-butoxyaluminum catalyst to obtain For dihydroartemisinin, the water phase was separated, and methanol, sodium bisulfate, aluminum perchlorate, nickel perchlorate, etc. were added as catalysts for the etherification reaction. The highest total yield of artemether was 93.5%, but the obtained product The content of β-artemether in the

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  • Preparation method of artemether

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[0018] The invention discloses a preparation method of β-artemether. Those skilled in the art can refer to the content of this article and appropriately improve the process parameters to realize it. It needs to be pointed out that all similar replacements and modifications are obvious to those skilled in the art, and they are all considered to be included in the present invention, and relevant personnel can obviously make changes without departing from the content, spirit and scope of the present invention. Changes or appropriate changes and combinations are made to the content described herein to realize and apply the technology of the present invention.

[0019] In the present invention, unless otherwise specified, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art.

Embodiment 1

[0022] Dissolve 100g (0.35mol) of artemisinin in 1L of methanol, cool down to -2°C, slowly add 40g (1.1mol) of sodium borohydride under stirring, monitor the progress of the reaction by TLC, wait for the reaction to end, naturally rise to room temperature, drop Add saturated ammonium chloride solution to neutralize until neutral, extract three times with 200mL dichloromethane, wash with water, and dry over anhydrous sodium sulfate;

[0023] Cool the above organic solution to -2°C, add 22g (0.21mol) trimethyl orthoformate, stir for 30min, add dropwise 35mL (about 0.07mol) of 30% boron trifluoride ether solution in ether, after the dropwise addition is complete, continue the reaction 1 hour, naturally rise to room temperature, monitor the reaction progress, after the reaction is completed, slowly add saturated sodium bicarbonate solution dropwise, adjust the system to neutral, separate the liquid, extract the aqueous phase twice with 50mL dichloromethane, combine the organic phas...

Embodiment 2

[0026] Dissolve 100g (0.35mol) of artemisinin in 1L of methanol, cool down to -2°C, slowly add 45g (0.83mol) of potassium borohydride under stirring, monitor the progress of the reaction by TLC, wait for the reaction to end, naturally rise to room temperature, drop Add saturated ammonium chloride solution to neutralize until neutral, extract three times with 200mL dichloromethane, wash with water, and dry over anhydrous sodium sulfate;

[0027] Cool the above organic solution to -2°C, add 21g (0.20mol) of trimethyl orthoformate, stir for 30min, add dropwise 35mL (about 0.07mol) of 30% boron trifluoride ether solution in ether, after the dropwise addition is complete, continue the reaction 1 hour, naturally rise to room temperature, monitor the reaction progress, after the reaction is completed, slowly add saturated sodium bicarbonate solution dropwise, adjust the system to neutral, separate the liquid, extract the aqueous phase twice with 50mL dichloromethane, combine the organ...

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Abstract

The invention discloses a preparation method of artemether, wherein the preparation method mainly includes three steps: step 1), artemisinin hydrogenation; step 2), etherification of dihydroartemisinin; and step 3), crude product purification. Through the three steps, an artemether refined product can be prepared, and the content of beta-artemether is high. The method has the advantages of simpleand practical process, high utilization rate of reaction raw materials, and high purity of the product, and is favorable for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of artemether, which belongs to the field of pharmaceutical chemical synthesis. Background technique [0002] Malaria, commonly known as Dabaizi and Dalaozhang, is a global acute parasitic infectious disease caused by Plasmodium, transmitted by Anopheles mosquitoes, and its unique symptoms are intermittent chills and fever. Worldwide, there are between 300 million and 500 million clinical cases each year, and malaria kills between one and three million people each year, most of them children. Children, pregnant women, tourists and new immigrants from all over the world have poor immunity to the locally prevalent malaria parasites, so they are high-risk groups susceptible to malaria. The main endemic areas of malaria are the tropical areas of central Africa, South Asia, Southeast Asia and northern South America, among which the epidemic situation in Africa is the worst. [0003] Artemether (English name Ar...

Claims

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Application Information

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IPC IPC(8): C07D493/20
CPCC07D493/20
Inventor 宋德成
Owner TIANJIN PACIFIC PHARMA
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