Preparation of 4-fluoroazetidinones using FClO.sub.3

Details Preparation of 4-fluoroazetidinones using FClO.sub.3 Preparation of 4-fluoroazetidinones using FClO.sub.3

1982-12-27

1985-02-19

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602454, 2603303, 2603309, 546208, C07D20508, C07D40104, C07D40304, C07B 900

Patent

active

045004560

ABSTRACT:
4-Fluoroazetidinone antibacterial agents are provided by a process comprising the reaction of an azetidinone-4-sulfinic acid, or a salt thereof, with perchloryl fluoride (FClO.sub.3) at -80.degree. C. to -25.degree. C., e.g., p-nitrobenzyl 3-methyl-2-(2-oxo-4-sulfino-3-phenoxyacetamido-1-azetidinyl-3-butenoate is reacted with FClO.sub.3 to provide corresponding 4-fluoroazetidinone. The latter is isomerized with a tertiary amine to corresponding 2-butenoate which a carboxy group deprotection provides an antibacterial compound.

REFERENCES:
patent: 4013653 (1977-03-01), Wolfe
patent: 4159984 (1979-07-01), Yoshioka et al.
patent: 4234724 (1980-11-01), Hashimoto et al.
Spitzer et al., J. Amer. Chem. Soc. 46, 3568 (1981).
Russian Journal of Organic Chemistry.

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