A kind of method for synthesizing azithromycin

A technology for azithromycin and erythromycin oxime, which is applied in the field of synthesizing azithromycin, can solve the problems of low yield, high requirements for hydrogenation reaction personnel operation and equipment conditions, etc., and achieves the effects of improving purity, shortening acidification and holding time, and reducing damage

Active Publication Date: 2021-07-16
杭州臻峰科技有限公司
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  • Application Information

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Problems solved by technology

Although the color and purity of the azithromycin produced in this way meet the market requirements, the yield is low, and the hydrogenation reaction has high requirements for personnel operation and equipment conditions

Method used

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  • A kind of method for synthesizing azithromycin

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Embodiment 1

[0027] Add 44 grams of erythromycin oxime, add 300 grams of water, add 15 grams of methanesulfonyl chloride dropwise under 5 degrees, control the pH to 3-4 during the dropping process (PH is too low, add baking soda), and add 30 grams of Dichloromethane was extracted once, and the aqueous layer was added dropwise with 85 g of 7% potassium borohydride aqueous solution (prepared and used now) in four drops, each time for 10 minutes. After dripping and keeping warm for 1.5 hours to pass, add 300 grams of dichloromethane, adjust the pH to 9, separate layers, extract the water layer with 20 grams of dichloromethane once, combine the organic layer, wash the organic layer until the pH reaches 8, add 3% sorbic acid 300 grams of sugar alcohol aqueous solution, reduce to 5 degrees, drop 6% dilute hydrochloric acid within 5 minutes to adjust the pH to 1, keep warm for 3 minutes, add 20% liquid alkali dropwise within 5 minutes to adjust the pH to 10, separate layers, and wash the organic l...

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Abstract

The invention discloses a method for synthesizing azithromycin. Using erythromycin thiocyanate as the starting material, after oximation, free erythromycin oxime is obtained, and the rearrangement, reduction, acidification and methylation reactions are directly carried out to obtain azithromycin. The whole reaction is carried out in one pot; the rearrangement reaction is qualified Then add a small amount of organic solvent to extract once, and directly carry out the reduction reaction. The reduction reaction reagent is potassium borohydride aqueous solution, and the configuration method of potassium borohydride solution is a small amount of multiple times at low temperature. To 9, separate layers, wash the organic layer once, add sorbitol aqueous solution, quickly add hydrochloric acid dropwise at low temperature until the pH is 1 for acidification, and after holding the heat for three minutes, quickly add liquid caustic soda dropwise until the pH is 10. After washing with water, azithromycin was obtained through methylation reaction. The whole reaction route of the present invention is relatively mild, the product color is white, the purity is high, the yield is high, the pollution is small, and the product is suitable for industrialized production.

Description

technical field [0001] The invention belongs to macrolide drugs, in particular to a method for synthesizing azithromycin. Background technique [0002] Azithromycin is the main representative variety of the second-generation erythromycin and has been widely used in the market. The traditional process mainly has two process routes: one is to take out the rearrangement, and the reduction reaction uses hydrogenation instead of potassium borohydride solution. Although the color and purity of the azithromycin produced in this way meet the market requirements, the yield is low, and the hydrogenation reaction has high requirements for personnel operation and equipment conditions. The second is a one-pot method to directly perform a reduction reaction on the rearrangement. The reduction reaction uses a potassium borohydride solution. After the reduction is completed, it is acidified with hydrochloric acid for a long time, and then the alkali is adjusted to remove the boride. Becau...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H1/00C07H17/00
CPCC07H1/00C07H17/00
Inventor 张更真张国庆
Owner 杭州臻峰科技有限公司
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