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Preparation method of artemether impurity dehydrated dihydroartemisinin

A technology of dihydroartemisinin and methanol aqueous solution, which is applied in the direction of organic chemistry, can solve the problems of complex process flow, low single-pass conversion rate of reactants, and low production efficiency, and achieve good process safety, low cost, and simple operation Effect

Active Publication Date: 2022-04-05
ZHANG JIA GANG VINSCE BIO PHARM
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  • Description
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Problems solved by technology

At present, in the synthesis process of dehydrated dihydroartemisinin, chemical reagents such as phosphorus oxychloride and triethylamine are often used in the reaction process, and the post-treatment is separated and purified by silica gel column chromatography, which makes the process complicated and there is a one-way process of reactants. Disadvantages such as low conversion rate and low production efficiency

Method used

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preparation example Construction

[0037] In some specific embodiments, the present invention provides a method for preparing dehydrated dihydroartemisinin, which comprises:

[0038] Dissolve a certain amount of dihydroartemisinin in an appropriate amount of organic solvent, cool down to 0°C-5°C, and add boron trifluoride ether to the solution under stirring;

[0039] After the solution is clarified, continue to stir for 10-30 minutes; then stand at room temperature in the dark for a period of time;

[0040] After the reaction is completed, the reaction solution is extracted and concentrated to obtain the crude product of dehydrated dihydroartemisinin;

[0041] Purify the crude dehydrated dihydroartemisinin to obtain dehydrated dihydroartemisinin.

[0042] According to a specific embodiment of the present invention, the organic solvent in the present invention includes one of acetone, methylene chloride, chloroform, carbon tetrachloride, tetrahydrofuran, diethyl ether and petroleum ether or a mixed solvent com...

Embodiment 1

[0062] Take 28.4g of dihydroartemisinin Artemisia annua, add it to 568mL (mass volume ratio 1:20) of dichloromethane solvent, stir and cool down to 0°C (in an ice bath);

[0063] After continuous stirring for 20 minutes, add 85.2 mL of boron trifluoride diethyl ether dropwise to the above solution, and continue stirring for 15 minutes after the solution is clarified;

[0064] Then the reaction flask was taken out from the ice bath, wrapped with aluminum foil for shading and allowed to stand at room temperature for 48 hours, TLC monitoring confirmed that the reaction was complete.

[0065] The reaction solution was successively filled with 113.6mL of 10% NaHCO 3 Aqueous solution, 113.6mL saturated brine, and 113.6mL tap water were washed and extracted once respectively. When using aqueous sodium bicarbonate solution for extraction, the operation method adopted is to put the aqueous solution of sodium bicarbonate in a beaker, and slowly pour into the reaction solution under the...

Embodiment 2

[0068] Take 28.4g of dihydroartemisinin Artemisia annua, add it to 568mL (mass volume ratio 1:20) of dichloromethane solvent, stir and cool down to 0°C (in an ice bath);

[0069] After continuous stirring for 20 minutes, add 85.2 mL of boron trifluoride diethyl ether dropwise to the above solution, and continue stirring for 15 minutes after the solution is clarified;

[0070] Then the reaction flask was taken out from the ice bath, wrapped with aluminum foil for shading and allowed to stand at room temperature for 48 hours, TLC monitoring confirmed that the reaction was complete.

[0071] The reaction solution was successively washed with 75.7mL of 10% NaHCO 3 Aqueous solution, 75.7mL saturated saline, 75.7mL tap water were washed and extracted once respectively. When using aqueous sodium bicarbonate solution for extraction, the operation method adopted is to place the aqueous solution of sodium bicarbonate in a beaker, and slowly pour into the reaction solution under the con...

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Abstract

The invention discloses a preparation method of artemether impurity dehydrated dihydroartemisinin, and belongs to the technical field of medicinal chemistry. Specifically, the preparation method provided by the invention comprises the following steps: dissolving a certain amount of dihydroartemisinin in a proper amount of an organic solvent, cooling to 0-5 DEG C, and adding boron trifluoride diethyl etherate into the solution under a stirring condition; after the solution is clarified, continuously stirring for 10-30 minutes; standing in a dark place at room temperature; after the reaction is completed, extracting and concentrating reaction liquid to obtain a dehydrated dihydroartemisinin crude product; and purifying the dehydrated dihydroartemisinin crude product to obtain the dehydrated dihydroartemisinin. The preparation method provided by the invention has the advantages of high reaction efficiency and good process safety, does not need to use a large number of organic reagents, is lower in cost, meets the requirements of green chemistry, and is more suitable for large-scale production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry. Specifically, the present invention relates to a method for preparing dehydrated dihydroartemisinin as an impurity of artemether. Background technique [0002] β-artemether is a raw material drug, and ensuring drug safety and effectiveness is a basic principle to be followed in drug research and development and drug evaluation, and stable and controllable drug quality is the premise and basis for ensuring drug safety and effectiveness. Impurity research is an important part of drug quality research. It is closely related to process development, quality research, stability research, pharmacology and toxicology and clinical research, and is directly related to the quality and safety of marketed drugs. In order to ensure the quality of raw materials, the products must meet the corresponding quality standards. Different countries have different requirements for drug registration, which is not con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20
CPCY02A50/30
Inventor 彭学东张梅赵金召刘长青
Owner ZHANG JIA GANG VINSCE BIO PHARM
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