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Synthesis method of eto-tilmicosin

A technology based on tilmicosin and tilmicosin, applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve problems affecting product quality, low water content in acetone, damage to tilmicosin, etc. problems, to achieve the effect of low water content requirements in solvents, easy filtration, and reduced production costs

Inactive Publication Date: 2014-07-16
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] First; the reaction solvent acetone must ensure that the water content is very low, and the requirements for the solvent are strict, resulting in high production costs;
[0006] Second: Use potassium carbonate for desulfurization, and repeatedly use potassium carbonate for dehydration, adsorption and filtration in the desulfurization process, the process is complicated and the cost is high;
[0007] Thirdly, using potassium carbonate for desulfurization, the alkalinity of the system is high, and it is easy to destroy tilmicosin (tilmicosin is easy to remove a sugar group --- de sugar group when the pH is ≥ 11), which affects product quality;

Method used

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  • Synthesis method of eto-tilmicosin

Examples

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Embodiment 1

[0032] 1) Add 20g of water and 50g of tilmicosin thiocyanate to 140g of acetone, raise the temperature to 35~38°C, stir for 5 minutes, then add 9g of triethylamine to desulfurize tilmicosin thiocyanate into free tilmicosin Star base, system clarification;

[0033] 2) Add 13.5g propionic anhydride to the system obtained in step 1), react at 35~38°C for 120 minutes to generate tilmicosin propionate, and then filter;

[0034] 3) Add dodecyl sulfate solution to the filtrate obtained in step 2) (dodecyl sulfate solution is prepared as dodecyl sulfate: water = 17g : 90g), and react at 35~38°C 60 minutes to generate eptotilmicosin;

[0035] 4) Add 50g of water to the solution obtained in step 3) at 35~38°C to make the solution turbid, stir for 60 minutes to precipitate a large amount of ettotilmicosin; then add 500g of water to cool down to 5~10°C for 60 minutes to crystallize , centrifuged, and the filter cake was washed with water and dried, and 61 g of ettotilmicosin was isolate...

Embodiment 2

[0037] 1) Add 28g of water and 50g of tilmicosin thiocyanate to 175g of acetone, raise the temperature to 38~42°C, stir for 10 minutes, then add 8g of triethylamine to desulfurize tilmicosin thiocyanate into free tilmicosin Star base, system clarification;

[0038] 2) Add 15g of propionic anhydride to the system obtained in step 1), react at 38~42°C for 120 minutes to generate tilmicosin propionate, and then filter;

[0039] 3) Add dodecyl sulfate solution to the filtrate obtained in step 2) (dodecyl sulfate solution is prepared as dodecyl sulfate: water = 19g : 100g), and react at 38~42°C 40 minutes to generate eptotilmicosin;

[0040] 4) Add 50g of water to the solution obtained in step 3) at 38~42°C to make the solution turbid, stir for 40 minutes to precipitate a large amount of ettotilmicosin; then add 400g of water to cool down to 5~10°C for 60 minutes to crystallize , centrifuged, and the filter cake was washed with water and then dried to isolate 62g ettotilmicosin, ...

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Abstract

The invention discloses a synthesis method of eto-tilmicosin. Tilmicosin sulfocyanide serving as a main raw material is desulfurated by using triethylamine in the presence of an acetone-water solvent and then is subjected to one-pot process together with propionic anhydride and lauryl sulfate, thus synthesizing eto-tilmicosin. The synthesis method has low requirement on the water content of the solvent, reduces the production cost and is convenient in recycling of the solvent; triethylamine, instead of potassium carbonate, is used for desulfuration, the operation that potassium carbonate is used repeatedly for dehydration, adsorption and filtration in the desulfuration process is omitted, the process is simplified, the production efficiency is improved, the production cost is lowered, the conditions are mild, the damage of strong alkaline condition on tilmicosin alkali is avoided, and the production quality is improved.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a synthesis method of ettotilmicosin. Background technique [0002] Tilmicosin is a macrolide semi-synthesized from tylosin, which is an antibiotic for animals. The chemical name of tilmicosin is 4A-O-de(2,6-dideoxy-3-C-methyl-L-ribose-pyranylhexyl)-20-deoxy-20-(3,5-dimethyl Base-1-piperidinyl)-[20 (cis:trans)]tylosin, also known as 20-deoxy-20-(3,5-dimethyl-1-piperidinyl) decarb Mycosyl Tylosin. Tilmicosin is a derivative of tylosin after acid hydrolysis, which is a semi-synthetic macrolide antibiotic. Tilmicosin reacts with 3,5-dimethylpiperidine to generate tilmicosin base, and then phosphoric acid and water are added to form tilmicosin phosphate. Tilmicosin has a broad-spectrum antibacterial activity similar to that of tylosin, both of which are effective against Gram-negative bacteria, Pasteurella avium multocida, Erysipelothrix rhusiopathiae, Actinob...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00A61P31/04
Inventor 李逐波周凯何小燕左华赵晓燕
Owner SOUTHWEST UNIV
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