Method for synthesizing and purifying tulathromycin impurity E

A technology of telamycin and impurities, which is applied in the field of medicinal chemistry, can solve the problems of low purity of telamycin impurity E, unsatisfactory structure and properties, and difficult control of the synthesis process, so as to improve purity, promote conversion efficiency, and improve properties. stable effect

Inactive Publication Date: 2021-01-15
JIANGSU WEI LING BIOCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] 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

Method used

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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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Effect test

Embodiment 1

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

[0042] (1) Add 3.0g of potassium hexamethyldisilazide, 100ml of DMSO and tetrahydrofuran to a 500ml four-necked flask, stir to dissolve, pass N2 for protection, add 15.7g of trimethylsulfoxide iodide in stages, and control the temperature to 0 ℃, keep stirring at this temperature for 2 hours; add DMSO solution of teramycin oxide (30g+100ml) dropwise, control the dropping temperature at 30 ℃, after the dropwise addition, keep the reaction at -50 ℃ for 1 hour, take samples for detection , epoxy idene ketone isomer: epoxy compound = 85:15, the reaction solution was added to 10% ammonium chloride aqueous solution to quench the reaction, the reaction solution was layered, washed with brine, and the organic phase was concentrated to dryness to obtain a ring 30.4 g of crude oxalide isomer;

[0043] (2) Refining the crude epoxy ketone isomer: dissolve the c...

Embodiment 2

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

[0049] (1) To a 500ml four-necked flask, add 3.0g of sodium hydride, 100ml of DMSO and tetrahydrofuran in total, stir to dissolve, pass in N2 for protection, add 15.7g of trimethyl sulfoxide iodide in stages, control the temperature to 20°C, and keep the temperature at this temperature. Stir for 2 hours; add DMSO solution of teramycin oxide (30g+100ml) dropwise, control the dropwise temperature at -30°C, keep the temperature at -50°C for 1 hour after the dropwise addition, take samples for detection, epoxy alkenone Isomer: epoxy compound = 90:10, the reaction solution was added to 10% ammonium chloride aqueous solution to quench the reaction, the reaction solution was separated into layers, washed with brine, and the organic phase was concentrated to dryness to obtain epoxy idene ketone isomerization Crude product 31.4g;

[0050] (2) Refining the cr...

Embodiment 3

[0055] The method for synthesizing and purifying teramycin impurity E of the present embodiment comprises the following steps:

[0056] (1) To a 500ml four-necked flask, add 3.0g of sodium hydride, a total of 100ml of DMSO and tetrahydrofuran, stir and dissolve, pass into N2 for protection, add 15.7g of trimethyl sulfoxide iodide in stages, control the temperature to 10°C, and keep the temperature at this temperature. Stir for 2 hours; add DMSO solution of teramycin oxide (30g+100ml) dropwise, control the temperature of dropwise addition at 0°C, and keep the temperature at -50°C for 1 hour after the dropwise addition is completed. Structure: epoxy compound = 90:10, the reaction solution was added to 10% ammonium chloride aqueous solution to quench the reaction, the reaction solution was separated into layers, washed with brine, and the organic phase was concentrated to dryness to obtain epoxyidene ketone isomers Crude product 30.0g;

[0057] (2) Refining the crude epoxy keton...

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Abstract

The invention discloses a method for synthesizing and purifying a tulathromycin impurity E. In the epoxidation process, an isomer of an epoxy compound is obtained by adjusting raw materials and reaction temperature, and the required tulathromycin E is obtained by the steps of removing a protecting group, aminating and the like. According to the method for synthesizing and purifying the tulathromycin impurity E, the problems that in the prior art, the purity of the tulathromycin impurity E is low, operation is complex, the synthesis process is not easy to control, the single-time preparation yield is low, and the research conditions for the structure and properties of the tulathromycin impurity E cannot be met are solved, the raw materials and the reaction temperature are adjusted, trimethyl sulfoxide iodide is added into DMSO, and the thiourea reaction is promoted, so that the generated epoxy compound is mainly composed of an upright bond, the conversion efficiency of the tulathromycinimpurity E is promoted, and the purity of the tulathromycin impurity E is improved while a large amount of tulathromycin impurity E is generated.

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 teramycin. Background technique [0002] Talamycin (Tulathromye) is a semi-synthetic macrolide antibiotic for animals. It is mainly used for the respiration of pigs and cattle caused by Actinobacillus, Mycoplasma, Pasteurella, and Haemophilus paraben. Systemic diseases, it has many advantages such as less dosage, one-time administration, low residue and animal use. [0003] At present, the methods of teramycin A at home and abroad are mainly as follows: using azithromycin A as a raw material, obtaining azithromycin A protected by Cbz-Cl, and then oxidizing it by the improved Pfitznor-Moffat method to obtain a Cbz-protected ketone, and the ketone is protected by Wittig- Horner reaction, the ketone group is converted into an alkenyl group to obtain a protected alkene, the protected alkene is oxidized to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/00C07H1/06
CPCC07H17/00C07H1/06Y02P20/55
Inventor 凌青云张猛刘言华杨玲卫
Owner JIANGSU WEI LING BIOCHEM TECH CO LTD
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