ChemicalBook CAS DataBase List Florfenicol

Florfenicol synthesis

7synthesis methods

Product Name:Florfenicol
CAS Number:73231-34-2
Molecular formula:C12H14Cl2FNO4S
Molecular Weight:358.21

Florfenicol is synthesised from thiamphenicol by replacing the 3-hydroxy group with fluorine, first synthesised at Schering in 1980. By replacing the hydroxy group, it was rationalised that chloramphenicol resistance via chloramphenicol acetyltransferase could be eliminated. Florfenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. It acts by binding to the 23S sub-unit of the 50S ribosome, inhibiting protein synthesis. Florfenicol has been extensively studied with over 400 literature citations.

Oxazole, 2-(dichloromethyl)-4-(fluoromethyl)-4,5-dihydro-5-[4-(methylsulfonyl)phenyl]-, (4S,5R)-

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Yield:73231-34-2 99%

Reaction Conditions:

with hydrogenchloride in water;isopropyl alcohol at 70; pH=6; for 5 h;

Steps:

c.10

Take step b to obtain 34.02g (0.1mol) of compound III, and add it into a 250ml glass four-neck bottle,Add 70g of purified water and 75g of isopropanol, stir and mix, adjust the PH value to 6.0 with dilute hydrochloric acid, then heat to 70°C and keep hydrolyzing for 5.0h, and wait until the fluoride is completely hydrolyzed.Cool down to crystallize and keep at 05 to crystallize for 2h, filterThe white florfenicol was obtained, the weight was 35.46 g (0.099 mol), and the yield was 99.00%.

References:

CN112538034,2021,A Location in patent:Paragraph 0063-0065