Process for the preparation of 2-halomethyl-penems and their use

Details Process for the preparation of 2-halomethyl-penems and their use Process for the preparation of 2-halomethyl-penems and their use

1998-08-06

2000-11-28

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540357, C07D499887, C07D20509

Patent

active

061537470

ABSTRACT:
Process for the preparation of 2-halomethyl-penems (I) comprising (a) reacting an acetoxy-(protected hydroxyethyl)-2-azetidinone (III) with a 2-halothioacetic acid to form a 3-haloacetylthioazetidinone (V), (b) reacting (V) with oxalyl chloride to give an intermediate (VII), acylated on the beta-lactamic nitrogen, and (c) cyclizing (VII) in the presence of an organic phosphate or phosphonite to produce the corresponding 2-halomethyl-penem (I).

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Wise, Antimicrobial Newsletter 7(10), 73, Oct. 1990.
Pentassuglia, J. Antibiotics 48, 399, May 1995.
Altamura, J. Org. Chem 58, 272, Jan. 1993.
Arndt, Berichte 63, 2390, 1930.

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