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Application of fluorinating agent in florfenicol preparation technology

The technology of florfenicol and fluorinating agent is applied in the application field of fluorinating agent in the preparation process of florfenicol, which can solve the problems of high cost of fluorinating agent, difficulty in comprehensive utilization of tetrafluoropropionamide and the like, and achieve molecular weight Small, convenient for comprehensive utilization and low price

Inactive Publication Date: 2013-08-21
NANTONG JINLI OIL & FAT IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the factories that prepare florfenicol in large quantities, problems such as the high cost of the fluorinating agent and the difficulty in the comprehensive utilization of the by-product tetrafluoropropionamide (3) after the reaction have also been encountered.

Method used

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  • Application of fluorinating agent in florfenicol preparation technology
  • Application of fluorinating agent in florfenicol preparation technology
  • Application of fluorinating agent in florfenicol preparation technology

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] The fluorination experiment of embodiment 1 compound 5:

[0016] Reaction formula:

[0017]

[0018] Typical operation steps:

[0019] In a 1000 ml clean dry autoclave with magnetic stirring, sequentially add compound (5,50 g, 0.149 mol), solvent chloroform or dichloromethane (150 ml) and 0.238 mol of fluorinating agent (4a, 34.6 g; 4b, 41.3 g; 4c, 47.8 g), tighten the autoclave and close all valves. Start stirring and control the rotation speed at 50-80 rpm, slowly heat to 80-110°C, at this time the system pressure is below 0.9Mpa, and react for 30-60 minutes. Stop heating, keep the stirring speed at 30 rpm, and after the system temperature is lowered to room temperature, open the kettle and transfer the material liquid in the kettle to the hydrolysis reaction bottle, start stirring, and slowly add (8g of potassium fluoride, 42g of water) for fluorination Potassium aqueous solution, continue to react for 1 hour, stop the reaction. Recover chloroform or dichlorom...

Embodiment 2

[0023] The fluorination experiment of embodiment 2 compound 6:

[0024] Reaction formula:

[0025]

[0026] Typical operation steps:

[0027] In a 1000 ml clean dry autoclave with magnetic stirring, sequentially add compound (6,50 g, 0.153 mol), solvent dichloromethane or benzene (150 ml) and 0.245 mol of fluorinating agent (4a, 35.6 g; 4b, 41.5 g; 4c, 48.2 g), tighten the autoclave and close all valves. Start stirring and control the rotation speed at 50-80 rpm, slowly heat to 80-110°C, at this time, the system pressure is below 0.7Mpa, and react for 30-60 minutes. Heating was stopped, the stirring speed was kept at 30 rpm, and after the temperature of the system was lowered to room temperature, the kettle was opened and the material liquid in the kettle was transferred to a hydrolysis reaction bottle, and after the treatment according to the method of Example 1, the crude product of Florfenicol was obtained. The reaction results are shown in the table below:

[0028] ...

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PUM

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Abstract

The invention relates to an application of a fluorinating agent in a florfenicol preparation technology. Particularly, a fluoridation reaction is performed between a fluorinating agent and a florfenicol intermediate (4R, 5R)-2-(dichloromethyl) 4,5-dihydro-5-(4-methylsulfone phenyl)-4-oxazol methanol (5) or (4R, 5R)-3-acetyl-2,2-dimethyl-4-hydroxymethyl-5-(4-methylsulfone phenyl) oxazolidine (6), and then florfenicol is obtained by hydrolysis, wherein the fluorinating agent has the structural formula shown in the specification. The fluorinating agent is simple to prepare and is cheap; with small molecular weight, a small amount of the fluorinating agent is used; and a byproduct can be conveniently and comprehensively utilized.

Description

technical field [0001] The invention relates to the application of a fluorinating agent in the preparation process of florfenicol. Background technique [0002] Florfenicol (florfenical, 1) is a veterinary antibacterial drug developed and industrialized by Schering-Plough Animal Health in the United States (Syriopoulou V.P. et al., Antimicrob. Agents Chemother, 1980, 19, 294.). The mechanism of action of the compound is to tightly combine with the 50S of the 70S ribosome of the bacteria to prevent the synthesis of bacterial proteins, thereby having a bactericidal effect. This drug has broad-spectrum antibacterial activity, and has a good imitation effect on resistance to some other antibiotics (such as chloramphenicol, thiamphenicol, etc.), and can be used to treat Gram-negative and positive bacteria and Rickettsia It has a significant curative effect on bacterial respiratory system diseases of cattle, pigs, chickens, especially aquatic animals. Moreover, because the drug ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/32C07C315/04
Inventor 吴永明
Owner NANTONG JINLI OIL & FAT IND CO LTD
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