Preparation method of artemisinin

A technology of artemisinin and artemisinic acid, applied in the direction of organic chemistry and the like, can solve the problems of difficulty in realizing industrialized production, unsuitable for large-scale production, and low industrialization prospects, and achieves low cost, easy large-scale production, and simple post-processing. Effect

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

Due to the limitations of photochemistry itself, such as cumbersome operation, it is not suitable for large-scale production, so it is difficult to realize industrial production
Literature (Tetrahedron, 1986, 42, 819-828) reported the method of using (R)-(+)-vanillin as a raw material to synthesize artemisinin. However, due to the long synthetic route, the total yield is low and the atom economy is poor.
In addition, photochemical methods are also used to introduce peroxygen bonds, which is difficult to achieve industrial production
Others such as Mitchell A.Avery (J.Am.Chem.Soc., 1992.114.974-979) reported the utilization of pulegone as a raw material to synthesize artemisinin, which has a long synthetic route and low yield
At the same time, ozone is used to introduce peroxygen bonds, which is difficult to operate, poor in safety, and has low industrialization prospects.
If the traditional chemical synthesis method can be used to realize the introduction of the peroxy bond, not only the operability is strong, but also the experimental industrial production is very possible

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[0019] The invention discloses a preparation method of artemisinin, and those skilled in the art can learn from 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.

[0020] 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

[0023] Dissolve 100 g (0.43 mol) of artemisinic acid in 800 mL of chloroform, and react overnight at room temperature with a hydrogen pressure of 1 bar and 1.5 g of palladium carbon as a catalyst, filter with diatomaceous earth, wash with chloroform, and recover the solvent under reduced pressure to obtain a solid product Dihydroartemisinic acid 99g (0.42mol), yield 98%.

[0024] Dissolve 100g (0.42mol) of dihydroartemisinic acid in 500mL of acetone, use 105g (0.44mol) of sodium molybdate as a catalyst, and slowly add 30% hydrogen peroxide dropwise at -10°C as an oxidizing agent 150mL (about 1.32mol ), reacted for 24 hours, filtered, extracted three times with 200mL dichloromethane, and the organic phase was dried over anhydrous sodium sulfate.

[0025] Take the above reaction solution, lower the temperature to 0°C, add 200g (0.55mol) copper trifluoromethanesulfonate, feed oxygen, monitor the reaction progress, after the reaction is completed, filter, rinse with dichloromethan...

Embodiment 2

[0027] Dissolve 100g (0.43mol) of artemisinic acid in 1000mL of tetrahydrofuran, at room temperature, hydrogen pressure 2bar, 5.5g of Raney nickel as a catalyst, react overnight, filter with diatomaceous earth, wash with ethyl acetate, and recover the solvent under reduced pressure, 96 g (0.41 mol) of solid product dihydroartemisinic acid was obtained, and the yield was 95%.

[0028] Dissolve 100g (0.42mol) dihydroartemisinic acid in 500mL isopropanol, use 105g (0.44mol) sodium molybdate as a catalyst, and slowly add 30% hydrogen peroxide dropwise at -10°C as an oxidizing agent 150mL (approx. 1.32mol), reacted for 24 hours, filtered, extracted three times with 200mL dichloromethane, and dried the organic phase with anhydrous sodium sulfate.

[0029] Take the above reaction solution, lower the temperature to 0°C, add 180g (0.50mol) copper trifluoromethanesulfonate, feed oxygen, monitor the reaction progress, after the reaction is completed, filter, rinse with dichloromethane, a...

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Abstract

The invention discloses a preparation method of artemisinin, wherein the preparation method comprise the steps: with artemisinic acid as a starting material, obtaining dihydroartemisinic acid under the hydrogen/metal catalyst action, then oxidizing dihydroartemisinic acid into arteannuic acid dihydrogen peroxide by hydrogen peroxide in the presence of sodium molybdate, and finally acting with oxygen under the catalysis of copper trifluoromethanesulfonate, to obtain the target product artemisinin with high yield. Compared with the prior art, the preparation method has the following advantages:the used reagents are cheap and easy to get, the synthetic route is short, the reaction selectivity is high, the preparation process is environmentally friendly, the operation and post-processing aresimple, the total yield is high, and the preparation method is suitable for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of artemisinin, which belongs to the field of organic drug synthesis. Background technique [0002] 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, such as dihydroartemisinin, artemether, artesunate and so on. These artemisinin drugs have low toxicity and strong anti-masochistic properties, and have been approved by the WTO as the first-choice drugs for the treatment...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20
CPCC07D493/20
Inventor 宋德成
Owner TIANJIN PACIFIC PHARMA
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