Process for 4-halomethyl-azetidinones by cyclization of O-acylhy

Details Process for 4-halomethyl-azetidinones by cyclization of O-acylhy Process for 4-halomethyl-azetidinones by cyclization of O-acylhy

1986-08-06

1988-06-14

Berch, Mark L.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

558263, 2605005H, C07D20508, C07D40304, C07D41304, C07B 3900

Patent

active

047512962

ABSTRACT:
A process for 4-halomethylazetidin-2-ones is provided which comprises mixing in an inert solvent a positive halogen reagent in the presence of a weak base with a .beta.,.gamma.-unsaturated O-acylhydroxamate of the formula ##STR1## wherein R is protected amino, lower alkyl or phenyl substituted lower alkyl, R.sub.2 is a substituent such as lower alkyl which may be substituted by formyl, hydroxy, halogen, etc., and R.sub.1 is alkoxy, benzyloxy, etc. When R is a protected amino group, the process provides cis-4-halomethylazetidin-2-ones, while when R is alkyl or phenylalkyl, the trans isomer is obtained. The 4-halomethylazetidinones are useful intermediates for known antibiotic compounds.

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Afzali-Ardakani, A. and Rapoport, H., J. Org. Chem., 45, 4817-4820, (1980).
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Mattingly, P. G. et al., J. Org. Chem., 1980, 45, 410-415.

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