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Synthesis method of tulathromycin residue marker

A turamycin and marker technology, which is applied in the field of synthesis of turamycin residue markers, can solve the problems of easy degradation reaction, unstable erythromycin A oxime, and many by-products, etc., and achieves low cost of raw materials. , the effect of easy availability of raw materials and high reaction yield

Inactive Publication Date: 2014-10-29
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction is carried out in acetic acid, and erythromycin A oxime is unstable in acid and prone to degradation reactions, so there are many by-products

Method used

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  • Synthesis method of tulathromycin residue marker
  • Synthesis method of tulathromycin residue marker
  • Synthesis method of tulathromycin residue marker

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Dissolve 100 g of erythromycin A(E) oxime in 400 mL of acetone and 400 mL of water, add 50 g of sodium bicarbonate, and under stirring, add 38 g of p-toluenesulfonyl chloride at 0°C (dropped within 10 min), continue to stir for 3 h, and use The course of the reaction was monitored by thin layer chromatography (TLC). After the reaction was completed, the pH of the solution was adjusted to 12 with 20% NaOH, raised to room temperature, and the reaction was stirred for 30 min. At this time, a white solid was formed, suction filtration, and the obtained product was dried in a vacuum drying box at 50 °C for 5 h to obtain red. Mycin A6,9-imine ether 95g, yield>95%, melting point 129~131℃.

Embodiment 2

[0044] Dissolve 19 g of erythromycin A6,9-imine ether in 200 mL of methanol, add 8 g of sodium borohydride in batches at -15°C, and stir for 12 h. After the reaction is completed, add 15 g of citric acid, stir to dissolve, and add 10% dropwise. Concentration of sulfuric acid solution until the pH value of the solution is 3, and continue to stir the reaction for 1h. After the reaction was completed, 20% sodium hydroxide was added, the pH of the solution was adjusted to be alkaline, a white solid was precipitated, and filtered to obtain 16.5 g of erythromycin with a yield of 87% and a melting point of 114-116°C.

Embodiment 3

[0046] (1) Dissolve 15 g of azithromycin prepared by the method of Example 2 in methanol solution, stir and dissolve at -5 °C, add 4 mol / L sulfuric acid to adjust the pH value of the solution to 1-2, react for 6 h, and the reaction is completed Then, the pH of the solution was adjusted to 8-9 with 20% sodium hydroxide, extracted three times with an appropriate amount of dichloromethane, the filtrate was collected, and concentrated to obtain 7.2 g of crude TUM with a yield of 62%.

[0047] (2) Put 7.2g of TUM crude product in a three-necked flask equipped with a spherical condenser, add 100mL of a mixed solution of acetone and petroleum ether, the volume ratio of acetone and petroleum ether is 8:1, stir and dissolve at 60 ° C for 2h, then Cool to 0~5℃ for recrystallization for 6h, filter, and dry the obtained product. According to this method, it was recrystallized twice, and the obtained solid was dried in a vacuum drying oven at 50°C for 5 hours to obtain 3.9 g of pure TUM wi...

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PUM

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Abstract

The invention belongs to the technical field of chemical synthesis, particularly a chemical synthesis method of a tulathromycin residue marker named 3-decladinosyl-9-deoxy-9-dihydro-9a-aza-9a-homoerythromycin A. The method is characterized by comprising the following steps: carrying out Beckmann rearrangement reaction on the raw material erythromycin A (E) oxime to obtain erythromycin A 6,9-imino ether, reducing with sodium borohydride to obtain nitroerythromycin, hydrolyzing under acidic conditions to remove cladinose to obtain a 3-decladinosyl-9-deoxy-9-dihydro-9a-aza-9a-homoerythromycin A crude product, and repeatedly recrystallizing to obtain the pure product of which the HPLC (high performance liquid chromatography) purity is up to higher than 99.5%. The method has the advantages of simple technique and high reaction yield. The product has high purity and can be used as a standard substance candidate of the tulathromycin residue marker.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing a teramycin residue marker. The chemical name of the metabolite is 3-decladine-9-deoxy-9-dihydro-9a-nitrogen Hetero-9a-Homoerythromycin A. Background technique [0002] Terramycin, trade name Ruikexin, is the latest animal-specific semi-synthetic macrolide antibiotic developed by Pfizer Animal Health Company. The use of this drug was first approved by the Ministry of Agriculture of my country in 2008. Turamycin is a broad-spectrum antibacterial drug with antibacterial activity against Gram-positive and Gram-negative bacteria, especially sensitive to pathogenic bacteria that cause swine respiratory diseases, such as Pasteurella hemolytica, Pasteurella hemorrhagicus Bacillus, Haemophilus somnifera, Mycoplasma, Actinobacillus pleuropneumoniae, Bordetella bronchiseptica, Haemophilus parasuis, etc., also have good antibacterial effect ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00
Inventor 袁宗辉赵雅潘源虎王玉莲黄玲利周波陶燕飞陈冬梅谢书宇王旭刘振利谢长清
Owner HUAZHONG AGRI UNIV
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