A kind of preparation method of dihydroartemisinic acid

A technology of dihydroartemisinic acid and artemisinic acid, applied in the direction of ozone oxidation to prepare carboxylic acid, organic chemistry, etc., can solve the problems of low reduction reaction temperature, high production energy consumption, long reaction time, etc., and achieve simple preparation process, The effect of reduced dosage and short reaction time

Active Publication Date: 2016-02-10
HUNAN KEYUAN BIO PRODS
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

But the reduction reaction temperature of this invention is on the low side, requires a cooling process, the production energy consumption is large, and the reaction time is long, and the amount of raw materials is large

Method used

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  • A kind of preparation method of dihydroartemisinic acid
  • A kind of preparation method of dihydroartemisinic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Dissolve 10g of artemisinic acid in 50ml of absolute ethanol, then add 6.5ml of 50% hydrazine hydrate and 3ml of an aqueous solution containing 200mg of guanidine nitrate, adjust the reaction temperature to 45°C, and feed oxygen into the reaction solution at a rate of 60ml / min After 4 hours of reaction, HPLC showed that the reaction was complete; adding 100ml of water, extracted twice with 50ml of methyl tert-butyl ether, dried the organic phase with anhydrous sodium sulfate, filtered, concentrated, and the obtained residue was crude dihydroartemisinic acid 11.0g, the purity was 90% as shown by HPLC.

Embodiment 2

[0030] Dissolve 2.34g of artemisinic acid in 10ml of absolute ethanol, then add 2ml of 40% hydrazine hydrate and 1ml of an aqueous solution containing 40mg of guanidine sulfate, adjust the reaction temperature to 55°C, and slowly and uniformly drop 30% of hydrogen peroxide 6.0 into the reaction solution ml, the dropwise addition process lasted for 4 hours; after the dropwise addition was completed, HPLC showed that the reaction had been completed after 3 hours of heat preservation reaction; 50ml of water was added, extracted twice with 30ml of methyl tert-butyl ether, and the organic phase was dried with anhydrous sodium sulfate. After filtration and concentration, the obtained residue was 2.4 g of crude dihydroartemisinic acid, the purity of which was 92% as shown by HPLC.

Embodiment 3

[0032] Dissolve 10g of artemisinic acid in 50ml of absolute ethanol, then add 6.5ml of 80% hydrazine hydrate and 5ml of aqueous solution containing 200mg of guanidine hydrochloride, adjust the reaction temperature to 50°C, and feed oxygen into the reaction solution at a rate of 120ml / min After 4 hours of reaction, HPLC showed that the reaction was complete; adding 100ml of water, extracted twice with 50ml of methyl tert-butyl ether, dried the organic phase with anhydrous sodium sulfate, filtered, concentrated, and the obtained residue was crude dihydroartemisinic acid 10.5g, the purity was 91.8% by HPLC.

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Abstract

A preparation method of dihydroartemisinic acid, the steps are as follows: dissolving artemisinic acid in an organic solvent, then adding any concentration of hydrazine hydrate and a catalytic amount of guanidine salt, adjusting the reaction temperature to 25°C to 100°C, and then Add any concentration of hydrogen peroxide dropwise to the reaction solution or pass in oxygen to generate diimine in situ, so that artemisinic acid is reduced to dihydroartemisinic acid by the diimine generated in situ, and dihydroartemisinic acid is obtained by extraction and drying to obtain dihydroartemisinic acid Artemisinic acid. The invention has low energy consumption, short reaction time, simple preparation process and high yield of dihydroartemisinic acid, and is suitable for large-scale industrial production.

Description

Technical field [0001] The present invention involves the preparation method of artemisinin intermediates, especially the preparation method of a miminal hydrogen artemisic acid in the intermediate of artemisininin. Background technique [0002] Artemisiainin is a compound with a semi -semi -cymbal ester with a peroxy bridge, which has anti -malaria effects. It is a mitochondrial function that interferes with the surface membrane -mitochondrial function of the Plasmonia.Some derivatives of artemisinin, such as bisroginhylinin, artemisia methar ether, have higher antimalarial efficacy. [0003] At present, artemisinin is mainly extracted from Artemisia annua (Artemisia annua).Global raw material Artemisia annua is mainly from Puyang, Chongqing, China, and the output of Artemisia annua is greatly affected by the environment and weather.At the same time, the planting of Artemisia annua requires a large area of land, and the extraction process consumes a large amount of organic solve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C57/26C07C51/36
CPCC07C51/36C07C2602/28C07C57/26
Inventor 林文彬刘志强
Owner HUNAN KEYUAN BIO PRODS
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