Preparation method of tildipirosin

A technology of tediloxine and tylosin, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc. The effect of few side reactions and mild reaction conditions

Pending Publication Date: 2021-07-16
HUBEI LONGXIANG PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The aldehyde group at the reaction site is easily destroyed during the hydrolysis process of this method, thus affecting the subsequent reaction

Method used

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  • Preparation method of tildipirosin
  • Preparation method of tildipirosin
  • Preparation method of tildipirosin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] (1) Primary hydrolysis

[0072] 80 g (0.079 mol) of tylosin phosphate was dissolved in 3000 mL of water, and 40 mL of sulfuric acid with a mass fraction of 20% was added to obtain a reaction solution with a pH value of 2. Heat the reaction solution to 35°C and keep it warm for 1h. After the liquid chromatography monitors the reaction is complete, cool down to room temperature, add 300mL butyl acetate to the reaction solution, add 24mL NaOH solution with a mass fraction of 30% under stirring to adjust the pH value to about 10 , separated after stirring, and the upper organic phase was taken to obtain a primary hydrolyzate. The organic phase directly enters the next reaction.

[0073] (2) Reductive amination

[0074] Add 7.5 g (0.088 mol) of piperidine and 5 g (0.108 mol) of formic acid to the organic phase obtained in (1), insulate and react at 70 ° C for 3 h, add 150 mL of hydrochloric acid solution with a mass fraction of 5% after cooling down to room temperature, an...

Embodiment 2

[0083] (1) Primary hydrolysis

[0084] 80 g (0.079 mol) of tylosin phosphate was dissolved in 3000 mL of water, and 42 mL of sulfuric acid with a mass fraction of 20% was added to obtain a reaction solution with a pH value of 2. Heat the reaction solution to 40°C and keep it warm for 1h. After the liquid chromatography monitors that the reaction is complete, cool down to room temperature, add 300mL of butyl acetate to the reaction solution, add 25mL of 30% NaOH solution under stirring, and adjust the pH value to about 10. After stirring, separate the liquids, take the upper organic phase, and obtain the primary hydrolyzate. The organic phase directly enters the next reaction.

[0085] (2) Reductive amination

[0086] Add 7.6g (0.089mol) of piperidine and 5g (0.108mol) of formic acid to the organic phase obtained in (1), insulate and react at 70°C for 3h, add 150mL mass fraction of 5% hydrochloric acid solution after cooling to room temperature, and adjust the pH value to abo...

Embodiment 3

[0095] (1) Primary hydrolysis

[0096] 81 g (0.079 mol) of tylosin phosphate was dissolved in 3000 mL of water, and 42 mL of sulfuric acid with a mass fraction of 20% was added to obtain a reaction solution with a pH value of 2. Heat the reaction solution to 40°C and keep it warm for 1 hour. After the liquid chromatography monitors that the reaction is complete, cool down to room temperature, add 300mL of butyl acetate to the reaction solution, add 26mL of 30% NaOH solution under stirring, and adjust the pH value to about 11. After stirring, separate the liquids, take the upper organic phase, and obtain the primary hydrolyzate. The organic phase directly enters the next reaction.

[0097] (2) Reductive amination

[0098] Add 7.6g (0.089mol) piperidine and 5g (0.108mol) formic acid to the organic phase obtained in (1), insulate and react at 70°C for 3h, add 150mL mass fraction of 5% hydrochloric acid solution after cooling to room temperature, and adjust the pH value to about...

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Abstract

The invention provides a method for preparing tildipirosin, which comprises the following steps of: performing a primary hydrolysis reaction on tylosin or salt thereof in an acid solution with the pH value of 1-3 to generate a compound as shown in a formula 1; performing a reductive amination reaction on the compound as shown in the formula 1 and piperidine under the condition of existence of a reducing agent to generate a compound as shown in a formula 2; performing a secondary hydrolysis reaction on the compound as shown in the formula 2 in an acid solution to generate a compound as shown in a formula 3; performing a sulfonic acid esterification reaction on the compound as shown in the formula 3 and a sulfonic acid esterification reagent to generate a compound as shown in a formula 4; and performing an amination reaction on the compound as shown in the formula 4 and piperidine to generate the tildipirosin. The method is mild in reaction condition, has few side reactions, is high in yield, low in cost, simple to operate, and suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a new preparation method of tedrol. Background technique [0002] Tildipirosin is a semi-synthetic macrolide antibiotic, a derivative of tylosin. The new CAS number of Tedilol 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, soluble in polar organic solvents (such as methanol, acetone, etc.), slightly soluble in water. [0003] Tedirosin is a broad-spectrum antibacterial drug, which has antibacterial activity against some Gram-positive and Gram-negative bacteria, and is particularly sensitive to pathogenic bacteria that cause respiratory diseases in pigs and cattle, such as Actinobacillus pleuropneumoniae, multocida Pasteurella, Bordetella bronchiseptica, Haemophilus parasuis, Mannheimia haemolytica, Histophilus somnus, etc. are used to prevent and treat respiratory infectious diseases in pigs and ca...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00
CPCC07H17/08C07H1/00
Inventor 胡争朋王铭宏
Owner HUBEI LONGXIANG PHARMA TECH CO LTD
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