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Tildipirosin preparation method

A technology of Tedirosin and Tylenolactone, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve problems such as strict operating conditions, reduce operating steps, reduce steps, and reduce costs Effect

Inactive Publication Date: 2016-03-09
TIANJIN ZHONGSHENG TIAOZHAN BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this process still uses iodine and anhydrous conditions, and the operating conditions are strict

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Preparation of 23-hydroxy-5-0-mycaminosyl-tylonolide (Ⅱ)

[0030] Add 30g (32.7mml) tylomycin to 300ml water, stir and heat up to 35-40 degrees, slowly add 27.6g48% HBr (163.5mml), keep warm for 2h, detect that the raw material content is less than 2%, add 16.6 g48% HBr (98.1mml), warm up to 45-50 degrees, continue to stir for 5 hours, cool down to room temperature, extract twice with 180ml ethyl acetate, cool the water phase to 4-8 degrees, and use 5mol / L NaOH Adjust the pH of the solution to about 10, extract three times with 180ml of dichloromethane, combine the organic phases, dry, concentrate under reduced pressure, beat with 60ml of methyl tert-butyl ether, filter, and dry to obtain 14.1g of 23-hydroxy-5-0 -mycaminosyl-tylonolide, yield 72.3%.

[0031] (2) Preparation of 14-formyl-5-0-mycaminosyl-tylonolide (Ⅲ)

[0032] The 23-hydroxyl-5-O-mycaminosyl-tylonolide (58.6mml) of 35g, 12.1gNaNO2 (175.8mml), 3.0g acetic anhydride (29.3mmol) were added in the aceti...

Embodiment 2

[0036] (1) Preparation of 23-hydroxy-5-0-mycaminosyl-tylonolide (Ⅱ)

[0037] Add 30g (32.7mml) tylomycin to 300ml water, stir and heat up to 50-55 degrees, slowly add 22.1g48% HBr (130.8mml), keep warm for 2h, detect that the raw material content is less than 2%, add 22.1 g48% HBr (130.8mml), heat up to 50-55 degrees, continue to stir for 5 hours, cool down to room temperature, extract twice with 180ml ethyl acetate, cool the water phase to 4-8 degrees, and use 5mol / L NaOH Adjust the pH of the solution to about 10, extract three times with 180ml of dichloromethane, combine the organic phases, dry, concentrate under reduced pressure, beat with 60ml of methyl tert-butyl ether, filter, and dry to obtain 13.1g of 23-hydroxy-5-0 -mycaminosyl-tylonolide, yield 67.0%.

[0038] (2) Preparation of 14-formyl-5-0-mycaminosyl-tylonolide (Ⅲ)

[0039]The 23-hydroxyl-5-O-mycaminosyl-tylonolide (58.6mml) of 35g, 20.2gNaNO2 (293.0mml) 6.0g acetic anhydride (58.6mmol) are added in the 50ml ac...

Embodiment 3

[0043] (1) Preparation of 23-hydroxy-5-0-mycaminosyl-tylonolide (Ⅱ)

[0044] Add 30g (32.7mml) tylomycin to 300ml water, stir and heat up to 35-40 degrees, slowly add 44.1g48% HBr (261.6mml), keep warm for 2 hours, when the content of raw materials is detected to be less than 2%, add 16.6 g48% HBr (65.4mml), warm up to 40-45 degrees, continue to stir for 5h, cool down to room temperature, extract twice with 180ml ethyl acetate, cool the water phase to 4-8 degrees, and use 5mol / L NaOH Adjust the pH of the solution to about 10, extract three times with 180ml of dichloromethane, combine the organic phases, dry, concentrate under reduced pressure, beat with 60ml of methyl tert-butyl ether, filter, and dry to obtain 13.5g of 23-hydroxy-5-0 -mycaminosyl-tylonolide, yield 69.1%.

[0045] (2) Preparation of 14-formyl-5-0-mycaminosyl-tylonolide (Ⅲ)

[0046] 35g of 23-hydroxy-5-O-mycaminosyl-tylonolide (58.6mml), NaNO2 (1:2-5), acetic anhydride (1:0.2-1) were added to 30ml of acetic a...

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Abstract

The present invention provides a tildipirosin preparation method, tylosin as a starting reactant is used for preparation of 23-hydroxyl-5-O-mycaminose-tylosin lactone, 14-aldehyde-5-O-mycaminose-tylosin lactone is further prepared, and finally tildipirosin(IV) is prepared; by determining of reasonable oxidizing conditions, the use of expensive iodine can be avoided, the reaction conditions can be reduced; by controlling of the reaction conditions, two times of hydrolysis reaction can be performed in one pot, the operation steps can be reduced, the technical purpose of overall cost reduction can be achieved, and the method is less in step, simple in process, low in cost, and suitable for large-scale industrial production need.

Description

technical field [0001] The invention relates to a preparation method of a compound, especially a preparation method of tedirosin. Background technique [0002] Tildipirosin (Tildipirosin) is a derivative of tylosin, and its structural formula is as follows: [0003] [0004] Tedirosin is the latest macrolide semi-synthetic antibiotic for animals developed by foreign companies. On March 8, 2011, the European Commission for Veterinary Medicines (CVMP) approved the market authorization application of Intervet's sterile injection solution (trade name Zuprevo) with Tedirosin as the main component. The new CAS number of Taidiluo is 328898-40-4, and the molecular formula is C 41 h 71 N 3 o 8 , molecular weight 734.02, melting point 192°C. [0005] At this stage, the new preparation methods of tedrol include: [0006] (1) Patent US6514946, using 20,23-diiodo-5-0-mycaminosyl-tylonolide as raw material, acetonitrile as solvent, reacting with piperidine for 1 h at reflux temp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00
CPCC07H17/08C07H1/00
Inventor 余贵菊董泽武王勇崔志刚王建程雪娇姜淋洁张立会杨雪于小婷范庆增
Owner TIANJIN ZHONGSHENG TIAOZHAN BIOTECH
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