Tulathromycin intermediate, preparation method of tulathromycin intermediate and preparation method of tulathromycin

A telamycin and intermediate technology, applied in the field of veterinary antibiotics, can solve the problems of expensive raw materials and harsh reaction conditions, and achieve the effects of reducing production costs, easy separation, and cost reduction

Inactive Publication Date: 2014-05-07
QINGDAO VLAND BIOTECH INC
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  • Abstract
  • Description
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Problems solved by technology

[0006] The invention provides a telamycin intermediate and its preparation method and the preparation method of telamycin, which can solve the problems of expensive ra

Method used

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  • Tulathromycin intermediate, preparation method of tulathromycin intermediate and preparation method of tulathromycin
  • Tulathromycin intermediate, preparation method of tulathromycin intermediate and preparation method of tulathromycin

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preparation example Construction

[0038] The synthetic method steps of telamycin intermediate and telamycin among the present invention are as follows:

[0039] 1. Synthesize key intermediates through protection, oxidation, epoxidation, deprotection, Beckmann rearrangement and reduction hydrolysis of erythromycin A(E) oxime;

[0040] 2. Put the telamycin intermediate and n-propylamine in isopropanol and use magnesium bromide as a catalyst to obtain telamycin that meets the quality standards. Its specific reaction route figure 1 shown.

Embodiment

[0042] Add erythromycin A(E) oxime (50 g, 0.067 mol), pyridine (5 g, ), dichloromethane (500 mL) into a 1L round-bottomed flask, stir vigorously in an ice-water bath, and slowly add acetic anhydride (16 mL , 0.17 mol) for about 45 min, TLC detection and reaction for 6 h, suction filtration, and drying to obtain a white solid, namely intermediate 1, with a yield of 100%.

[0043] Add intermediate 1 (50 g, 0.06 mol) into a 2L three-neck flask, protect it under nitrogen, inject DMSO (170 mL), heat to 60°C, slowly add acetic anhydride (110 mL, 1.2 mol) dropwise for about 1 hour, and maintain 60°C After reacting for 2 hours, after cooling, 100 mL of methanol was added to quench the reaction, concentrated under reduced pressure, a solid precipitated out, and dried to obtain a white solid, namely intermediate 2, with a yield of 90%.

[0044] Add trimethylsulfonium bromide (16.5 g, 0.11 mol) and anhydrous tetrahydrofuran (200 mL) into a 1L three-necked flask, cool to -20°C, add sodium h...

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Abstract

The invention provides a tulathromycin intermediate, a preparation method of the tulathromycin intermediate and a preparation method of tulathromycin. According to the preparation method, Erythromycin A (E) oxime used as a starting material is subjected to acetyl protection, Albright-Goldman oxidation, Corey-Chaykovsky epoxidation, deprotection, Beckmann rearrangement, reduction and hydrolysis, and n-propylamine ring opening to synthesize tulathromycin. The preparation method has mild conditions, has the advantages of convenient operation, high yield and low cost and is beneficial to industrial production, and the raw materials are easily available.

Description

[0001] technical field [0002] The invention belongs to the field of veterinary antibiotics, and in particular relates to a telamycin intermediate, a preparation method thereof and a telamycin preparation method. Background technique [0003] Respiratory tract infection is one of the most difficult diseases to control in animal husbandry, which seriously harms animal husbandry production. At present, macrolide antibiotics are a common class of drugs used to treat respiratory tract infections in pigs and cattle, such as tylosin and tilmicosin, which are widely used in my country. Although the use of these two drugs has achieved good results, with the prolongation of use time, drug resistance to varying degrees has appeared in many areas, and these two drugs are usually administered by mixing materials or drinking water. It takes repeated doses to be effective. Therefore, there is an urgent need in the market for novel antibacterial drugs that are highly effective, safe, br...

Claims

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Application Information

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IPC IPC(8): C07H19/01C07H17/00C07H1/00
Inventor 孙亚磊蒋贻海姚德勇贺倩倩侯青青
Owner QINGDAO VLAND BIOTECH INC
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