Method of semi-synthesizing artemisinin

A kind of artemisinin and semi-synthetic technology, applied in the direction of organic chemistry, etc., can solve the problems of increasing the number of repeated operations, the limitation of the size of the reactor, and the expensive price of the reactor, etc., and achieve the effect of short process flow and simple operation

Inactive Publication Date: 2013-05-08
HUNAN KEYUAN BIO PRODS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantage of this route is that the size of the reactor is limited to a certain extent, and the price of the reactor is expensive. To enlarge the production can only increase the number of repetitions of the operation

Method used

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  • Method of semi-synthesizing artemisinin
  • Method of semi-synthesizing artemisinin
  • Method of semi-synthesizing artemisinin

Examples

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example 1

[0023] Synthesis of Dihydroartemisinic Acid

[0024] Dissolve 14.0 grams of artemisinic acid in 100 ml of absolute ethanol, add 10 ml of 80% hydrazine hydrate at room temperature, cool the system to 0 degrees with an ice bath, and then slowly add 50% hydrogen peroxide to the reaction system 10mL, the dropwise addition process was over 1 hour. The reaction was then allowed to stir overnight at room temperature. The reaction system was acidified with dilute hydrochloric acid until the pH value was about 2, extracted with methyl tert-butyl ether, dried over anhydrous magnesium sulfate, and concentrated to obtain 14.2 g of dihydroartemisinic acid with a yield of 100%.

[0025] Synthesis of Dihydroartemisinic Acid Peroxyalcohol

[0026] Add 14.2 grams of dihydroartemisinic acid, 300 milliliters of ethylene glycol and 100 milligrams of Na 2 MoO 4 . The reaction system was stirred at 60°C, and then 19.2 ml of 30% hydrogen peroxide solution was slowly added to the reaction system...

example 2

[0030] Synthesis of Dihydroartemisinic Acid

[0031] Dissolve 14.0 grams of artemisinic acid in 100 ml of absolute ethanol, add 10 ml of 80% hydrazine hydrate at room temperature, cool the system to 0 degrees with an ice bath, and then slowly add 50% hydrogen peroxide to the reaction system 10mL, the dropwise addition process was over 1 hour. The reaction was then allowed to stir overnight at room temperature. The reaction system was acidified with dilute hydrochloric acid until the pH value was about 2, extracted with methyl tert-butyl ether, dried over anhydrous magnesium sulfate, and concentrated to obtain 14.3 g of dihydroartemisinic acid with a yield of 100%.

[0032] Synthesis of Methyl Dihydroartemisinate

[0033] Add 14.3 g of dihydroartemisinic acid into a single-necked bottle, then add 100 ml of saturated methanolic hydrogen chloride solution, and reflux overnight. Then the reaction system was concentrated to obtain 15.0 g of methyl dihydroartemisinate.

[0034] ...

example 3

[0039] Synthesis of Dihydroartemisinic Acid

[0040] Dissolve 14.0 grams of artemisinic acid in 100 ml of absolute ethanol, add 10 ml of 80% hydrazine hydrate at room temperature, cool the system to 0 degrees with an ice bath, and then slowly add 50% hydrogen peroxide to the reaction system 10mL, the dropwise addition process was over 1 hour. The reaction was then allowed to stir overnight at room temperature. The reaction system was acidified with dilute hydrochloric acid until the pH value was about 2, extracted with methyl tert-butyl ether, dried over anhydrous magnesium sulfate, and concentrated to obtain 14.2 g of dihydroartemisinic acid with a yield of 100%.

[0041] Synthesis of Dihydroartemisinic Acid Peroxyalcohol

[0042] Into a three-necked flask, 14.2 grams of dihydroartemisinic acid, 300 milliliters of acetonitrile, 2 milliliters of acetone and 2 grams of potassium hydroxide were successively added. 19.2 ml of 30% hydrogen peroxide solution was slowly added to ...

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Abstract

The invention relates to a method of semi-synthesizing artemisinin. The method comprises the steps of: reducing arteannuic acid into dihydro arteannuic acid by utilizing diimine produced in situ, oxidizing the dihydro arteannuic acid into peroxide alcohol by utilizing singlet oxygen produced in chemical reaction in situ, and then producing artemisinin under the action of oxygen and acid; or, obtaining dihydro arteannuic acid derivatives through protecting the dihydro arteannuic acid carboxyl, then oxidizing into corresponding peroxy alcohol under the action of the singlet oxygen produced in situ, and acting with the oxygen under the catalysis of acid to obtain artemisinin with high yield. A method of producing singlet oxygen in situ mainly comprises molybdate/peroxide, nitrile compound/peroxide, diacid iodobenzene/peroxide, peroxide-disulfate, and the like. With adoption of the method, the total yield can achieve up to 65%.

Description

technical field [0001] The invention relates to a preparation method of artemisinin, which belongs to the technical field of organic synthesis. technical background [0002] Artemisinin is a compound containing peroxy-sesquiterpene lactones extracted from the traditional Chinese medicine Artemisia annua. It is a highly effective and low-toxic antimalarial drug. It is of great interest to the world today and is the first internationally recognized natural drug. The antimalarial effect of artemisinin is by interfering with the membrane-mitochondria function of Plasmodium, which leads to the complete disintegration of the parasite structure. Some derivatives of artemisinin, such as dihydroartemisinin and artemether, have higher antimalarial efficacy. At present, the source of artemisinin is mainly extracted from the Chinese herbal medicine Artemisia annua. The main raw material of artemisinin in the world comes from Yiyang, Chongqing, China, and the production of artemisinin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20
Inventor 刘志强林文彬
Owner HUNAN KEYUAN BIO PRODS
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