Method for using tylosin D as raw material to prepare tilmicosin

A technology of tilmicosin and tylosin, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of high residual impurities and low yield, and achieve the effect of improving the utilization rate

Active Publication Date: 2017-06-30
QILU SYNVA PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method solves the problems of high residual impurities and low yield of tilmicosin prepared from tylosin as a starting material

Method used

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  • Method for using tylosin D as raw material to prepare tilmicosin
  • Method for using tylosin D as raw material to prepare tilmicosin
  • Method for using tylosin D as raw material to prepare tilmicosin

Examples

Experimental program
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Effect test

Embodiment 1

[0049]A method for preparing tilmicosin using tylosin D as a raw material, the steps are as follows:

[0050] (1) Add 91.8g of tylosin D into 500g of ethyl acetate, keep the temperature at 0-5°C, add 1.2gKBr, 0.8gTEMPO, 8.4g of sodium bicarbonate, stir well, slowly add dropwise 373g of 10% NaClO solution, and react After 4 hours, after the reaction was completed, the layers were separated, the water phase was discarded, and the organic phase was intermediate 1 ethyl acetate solution.

[0051] (2) Add 500g of purified water to the solution of intermediate 1 obtained in step (1), add 8.3g of hydrochloric acid, static layer, remove the organic phase, raise the temperature of the water phase to 50°C for reaction, and hydrolyze for 1.0h to obtain the intermediate 2;

[0052] (3) Add the aqueous solution of intermediate 2 obtained in step (2) to ethyl acetate, adjust the pH value to 8.0 with sodium hydroxide solution, separate the layers at rest, discard the water phase, and add 3,...

Embodiment 2

[0054] A method for preparing tilmicosin using tylosin D as a raw material, the steps are as follows:

[0055] (1) Add 91.8g of Tylosin D to 1000g of ethyl acetate, keep the temperature at 0-5°C, add 1.8gKBr, 1.2gTEMPO, 12.6g of sodium bicarbonate, stir evenly, slowly drop 560g of 10% NaClO solution, and react After 5 h, after the reaction was completed, the layers were separated, the water phase was discarded, and the organic phase was intermediate 1 ethyl acetate solution.

[0056] (2) Add 500g of purified water to the solution of intermediate 1 obtained in step (1), add 16.6g of hydrochloric acid, static layer, remove the organic phase, raise the temperature of the water phase to 50°C for reaction, and hydrolyze for 0.5h to obtain the intermediate 2;

[0057] (3) Add the aqueous solution of intermediate 2 obtained in step (2) to ethyl acetate, adjust the pH value to 10.0 with sodium hydroxide solution, separate the layers at rest, discard the water phase, and add 3,5-dimet...

Embodiment 3

[0059] A method for preparing tilmicosin using tylosin D as a raw material, the steps are as follows:

[0060] (1) Add 91.8g of tylosin D to 1500g of ethyl acetate, keep the temperature at 0-5°C, add 2.4gKBr, 1.8gTEMPO, 19.0g of sodium bicarbonate, stir evenly, slowly drop 746g of 10% NaClO solution, and react After 6h, after the reaction was completed, the layers were separated, the water phase was discarded, and the organic phase was intermediate 1 ethyl acetate solution.

[0061] (2) Add 500 g of purified water to the intermediate 1 solution obtained in step (1), add 24.9 g of hydrochloric acid, and separate the layers, remove the organic phase, raise the temperature of the water phase to 50 ° C for reaction, and hydrolyze for 0.5 h to obtain the intermediate 2;

[0062] (3) Add the aqueous solution of intermediate 2 obtained in step (2) to ethyl acetate, adjust the pH value to 12.0 with sodium hydroxide solution, separate the layers at rest, discard the water phase, and a...

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Abstract

The invention relates to a method for using tylosin D as a raw material to prepare tilmicosin. The method comprises the steps of using tylosin D as the raw material, oxidizing a C[20]position primary dydroxide radical into a formyl group through a selective oxidant to obtain a first midbody, then conducting hydrolysis and decarbonization on mycarose to obtain a second midbody, and making formic acid and 3,5 dimethyl piperidine subjected to a reductive ammonolysis reaction to obtain the product tilmcosin. According to the method for using tylosin D as the raw material to prepare tilmicosin, tylosin D is adopted as the raw material, through the specific selective oxidant, tylosin D is converted into an effective component in compound tilmicosin and is prevented from being converted into impurities, thus a new path is opened up for the preparation of tilmicosin, and the problems that the impurities are high in residual rate and the yield rate is low when tylosin is adopted as an original raw material to prepare tilmicosin are solved.

Description

technical field [0001] The invention relates to a method for preparing tilmicosin by using tylosin D as a raw material, belonging to the field of drug synthesis. Background technique [0002] Tilmicosin is a special macrolide antibiotic for livestock and poultry, mainly used to prevent livestock pneumonia, avian mycoplasma disease and mastitis of lactating animals. At present, the preparation method of tilmicosin is mainly based on phosphate or tartrate of tylosin as raw material, through acidic hydrolysis of mycose, and then reacting with 3,5-dimethylpiperidine to generate tilmicosin, Or change the reaction sequence, first react with 3,5-dimethylpiperidine and then hydrolyze to generate tilmicosin. For example, the preparation method of tilmicosin disclosed in Chinese patent document CN102382159 uses tylosin phosphate as raw material, alcohol as solvent, anhydrous formic acid as catalyst and 3,5-dimethyl Basepiperidine reaction, after the reaction is complete, the interme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00
CPCC07H1/00C07H17/08
Inventor 方明锋刘全才孔庆文孔梅吴连勇田振平
Owner QILU SYNVA PHARMA
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