Fragmentation procedure for preparing 3-amino-azetidinones

Details Fragmentation procedure for preparing 3-amino-azetidinones Fragmentation procedure for preparing 3-amino-azetidinones

1979-05-15

1981-09-08

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260465D, 2602454, 2603303, 2603473, 2603474, 542413, 542442, 542446, 542455, 560 29, 568426, C07D20508, C07D12000, C07D40306

Patent

active

042883644

ABSTRACT:
When 3-(2-hydroxyiminoacetylamino)-2-oxo-azetidine compounds are treated with reactive derivatives of carbonic acid half-esters in aqueous media in the presence of bases a fragmentation takes place which, in addition to 3-amino-2-oxo-azetidines, also yields nitriles which, compared with the 2-hydroxyiminoacetyl group, have one less carbon atom. The resulting products are intermediates for the preparation of nocardicin-like antibiotics.
The deacylation procedure of this specification offers advantages over the multi-stage deacylation procedure known hitherto, inasmuch as higher yields of 3-amino-2-oxoazetidine compounds are obtained and the acyl group can be obtained in the form of a nitrile which is shorter by one carbon atom.

REFERENCES:
Kunugita et al. Chem. Abs. 86, 153976y (1977).
Moroder et al., Chem. Abs. 86, 107005h (1976).

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