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A method for synthesizing and purifying Tyramycin impurity C

A technology of telamycin and impurity, which is applied in the field of synthesis and purification of telamycin impurity C, can solve the problems of low purity of telamycin impurity C, unsatisfactory structure and properties, and difficult control of the synthesis process, so as to achieve complete purification , stable properties and easy operation

Active Publication Date: 2020-05-08
JIANGSU WEI LING BIOCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides a method for synthesizing and purifying telamycin impurity C, which solves the problem of low purity of telamycin impurity C, complex operation, difficult control of the synthesis process, and single preparation yield in the production process of telamycin in the prior art Low, unable to meet the research conditions of its structure and properties

Method used

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  • A method for synthesizing and purifying Tyramycin impurity C
  • A method for synthesizing and purifying Tyramycin impurity C
  • A method for synthesizing and purifying Tyramycin impurity C

Examples

Experimental program
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Effect test

Embodiment 1

[0031] A. Put 20g of dry powder of Tyramycin into the container, add 200g of dichloromethane to dissolve, control the temperature at 30°C, add 2.0g of paraformaldehyde, 0.1g of tetrabutylammonium bromide, into a 500ml four-necked flask, and stir for 36 hours. ;

[0032] B, sampling detection, the residual amount of Tyramycin is 15%, continue to react for 14 hours; Sampling detection again, the residual amount of Tyramycin is 6.5%, further crystallize the reaction solution;

[0033] C. During crystallization treatment, add 200ml of water to the reaction solution, stir for 30 minutes, and separate layers; the dichloromethane layer is concentrated to dryness, add 50g of methanol to dissolve, add 100g of purified water dropwise, crystallize at 0°C for 2 hours, and extract the white crystals Filter and dry to obtain the crude product of Tyramycin impurity C;

[0034] D. Recrystallize the obtained Tyramycin impurity C crude product, add 30 g of acetone to dissolve 15 g of Tyramycin...

Embodiment 2

[0036] A. Put 20g of dry powder of Tyramycin into the container, add 200g of dichloromethane to dissolve, control the temperature at 30°C, add 5.0ml of formaldehyde, 1.5g of tetrabutylammonium bromide, into a 500ml four-necked flask, and stir for 24 hours;

[0037] B, sampling detection, the residual amount of Tyramycin is 14.5%, continue to react for 13 hours; Sampling and detection again, the residual amount of Tyramycin is 7%, and further crystallization is carried out to the reaction solution;

[0038] C. During crystallization, add 200ml of water to the reaction solution, stir for 30 minutes, and separate layers; the dichloromethane layer is concentrated and dried, add 50g of acetone to dissolve, add 100g of purified water dropwise, crystallize at 4°C for 2 hours, and filter the white crystals with suction , dried to obtain the crude product of Tyramycin impurity C;

[0039] D. Recrystallize the obtained Tyramycin impurity C crude product, add 30 g of acetone to dissolve ...

Embodiment 3

[0041] A. Put 20 g of dry powder of Tyramycin into the container, add 200 g of dichloromethane to dissolve, control the temperature at 40°C, put 2.0 g of paraformaldehyde, 2.0 g of tetrabutylammonium bromide in a 500 ml four-necked flask, and stir for 28 hours;

[0042] B, sampling detection, the residual amount of Tyramycin is 12.7%, continue to react for 12 hours; Sampling detection again, the residual amount of Tyramycin is 7.2%, and further crystallization is carried out to the reaction solution;

[0043] C. During the crystallization treatment, add 200ml of water to the reaction solution, stir for 30 minutes, and separate layers; Suction filtration of crystallization and drying to obtain the crude product of impurity C of Tyramycin;

[0044] D, recrystallize the obtained Tyramycin impurity C crude product, add 30g dichloromethane to dissolve 15g of Tyramycin C crude product, add dropwise 60g n-heptane, after the dropwise addition, white crystals are separated out, crystal...

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Abstract

The present invention discloses a method for synthesizing and purifying a tulathromycin impurity C. The method uses tulathromycin as a raw material, synthesizes the tulathromycin impurity C easy to beproduced in a production process of the tulathromycin, and facilitates studies of structures and properties of the impurity. The synthesized tulathromycin impurity C has stable properties and relatively high purity, and can meet research requirements of the structures and properties of the tulathromycin impurity in the industry. The method is easy to operate, synthesis is easy to control, and themethod meets quality control requirements of the impurity, uses methylene chloride as a solvent, uses paraformaldehyde or formaldehyde, enables reaction to be more thorough, and improves conversion efficiency of the tulathromycin under catalysis of trace tetrabutylammonium bromide. In a case of recrystallization, an appropriate ratio is used, so that a tulathromycin impurity C crude product is more complete in purification and purity of the tulathromycin impurity C crude product is improved.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a method for synthesizing and purifying impurity C of telamycin. Background technique [0002] Tulathromycin is a macrolide semi-synthetic antibiotic specially used for animals. Tulathromycin is mainly used for the breathing of pigs and cattle caused by Actinobacillus, Mycoplasma, Pasteurella and Haemophilus para For systemic diseases, it has many advantages such as less dosage, one-time administration, low residue and animal-specific. [0003] At present, the methods of Tyramycin A at home and abroad are mainly as follows: Azithromycin A is used as raw material, Azithromycin A is protected by Cbz-Cl, and then oxidized by the improved Pfitznor-Moffat method to obtain Cbz-protected ketone, and the ketone is passed through Wittig- Horner reaction, the ketone group is converted into an alkenyl group to obtain a protected alkene, and the protected alkene is o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/08C07H1/00
CPCC07H1/00C07H17/08
Inventor 凌青云张猛刘言华杨玲卫魏雅
Owner JIANGSU WEI LING BIOCHEM TECH CO LTD
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