Method for synthesizing and purifying tulathromycin impurity E

A technology of teramycin and impurities, applied in the field of medicinal chemistry, can solve the problems of low purity of tebramycin impurity E, unable to meet the structure and properties, difficult to control the synthesis process, etc., to improve the purity, promote the transformation efficiency, and improve the properties stable effect

Inactive Publication Date: 2019-03-29
JIANGSU WEI LING BIOCHEM TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The invention provides a method for synthesizing and purifying the impurity E of telamycin, which solves the problem of low purity, complicated operation, uneasy control of the synthesis process, low yield of single preparation and unsatisfactory structure of the impurity E of telamycin in the prior art. and questions of the nature of the research conditions

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  • Method for synthesizing and purifying tulathromycin impurity E
  • Method for synthesizing and purifying tulathromycin impurity E
  • Method for synthesizing and purifying tulathromycin impurity E

Examples

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Embodiment 1

[0034] The method for synthesizing and purifying telamycin impurity E of the present embodiment comprises the following steps:

[0035] (1) Add 3.0 g of potassium hexamethyldisilazide, 100 ml of DMSO and tetrahydrofuran to a 500 ml four-necked flask, stir to dissolve, and feed N 2 For protection, add 15.7 g of trimethylsulfoxide iodide in portions, control the temperature at 0° C., and keep stirring at this temperature for 2 hours; add the DMSO solution (30 g+100 ml) of telamycin oxide dropwise, and control the dropping temperature at 30°C, after the dropwise addition, keep it at -50°C for 1 hour, take a sample for detection, epoxy ketone isomer: epoxy compound = 85:15, add the reaction solution to 10% ammonium chloride aqueous solution, and quench the reaction , the reaction solution was layered, and after washing with brine, the organic phase was concentrated to dryness to obtain 30.4 g of the crude product of epoxy ketone isomers;

[0036] (2) The crude product of epoxy ke...

Embodiment 2

[0041] The method for synthesizing and purifying telamycin impurity E of the present embodiment comprises the following steps:

[0042] (1) Add 3.0 g of sodium hydride, 100 ml of DMSO and tetrahydrofuran to a 500 ml four-necked flask, stir and dissolve, and inject N 2For protection, add 15.7g of trimethylsulfoxide iodide in portions, control the temperature at 20°C, and keep stirring at this temperature for 2 hours; add the DMSO solution (30g+100ml) of telamycin oxide dropwise, and control the dropping temperature at -30°C, after the dropwise addition, keep it warm at -50°C for 1 hour, take a sample for detection, epoxy ketone isomer: epoxy compound = 90:10, add the reaction solution to 10% ammonium chloride aqueous solution, quench Reaction, the reaction solution was separated into layers, washed with brine, and then the organic phase was concentrated to dryness to obtain 31.4 g of the crude product of epoxy ketone isomers;

[0043] (2) The crude product of epoxy ketone isom...

Embodiment 3

[0048] The method for synthesizing and purifying telamycin impurity E of the present embodiment comprises the following steps:

[0049] (1) Add 3.0 g of sodium hydride, 100 ml of DMSO and tetrahydrofuran to a 500 ml four-necked flask, stir and dissolve, and inject N 2 For protection, add 15.7g of trimethylsulfoxide iodide in portions, control the temperature at 10°C, and keep stirring at this temperature for 2 hours; add the DMSO solution (30g+100ml) of telamycin oxide dropwise, and control the dropping temperature at 0°C, after the dropwise addition, keep it warm at -50°C for 1 hour, take a sample for detection, epoxy ketone isomer: epoxy compound = 90:10, add the reaction solution to 10% ammonium chloride aqueous solution, and quench the reaction , the reaction solution was layered, and after washing with brine, the organic phase was concentrated and dried to obtain 30.0 g of the crude product of epoxy ketone isomers;

[0050] (2) The crude product of epoxy ketone isomer is...

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Abstract

The present invention discloses a method for synthesizing and purifying a tulathromycin impurity E. In an epoxidation process, by adjusting raw materials and reaction temperatures, an epoxide isomer is obtained. Steps of protecting group removing, amination, etc. are conducted to obtain needed tulathromycin E. The method solves problems that in the prior art, the tulathromycin impurity E is low inpurity, operation is complicated, synthesis processes are not easy to control, single preparation is low in yield, and research conditions on structure and properties cannot be met. The method for synthesizing and purifying the tulathromycin impurity E adjusts the raw materials and reaction temperatures. Trimethylsulfoxonium iodide is added in DMSO to promote a sulfur ylide reaction, so that thegenerated epoxide is mainly composed of upright bonds. The method promotes conversion efficiency of the tulathromycin impurity E, thus generates a large amount of the tulathromycin impurity E and at the same time improves the purity of the tulathromycin impurity E.

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 E of telamycin. Background technique [0002] Tulathromycin (Tulathromycin) is a semi-synthetic macrolide antibiotic for animals. Tulathromycin is mainly used for respiratory problems in 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 a raw material, and Azithromycin A is protected by Cbz-Cl, and then oxidized by the improved Pfitznor-Moffat method to obtain a 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 prote...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00
CPCC07H1/00C07H17/08Y02P20/55
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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