Process for the preparation of 3-hydroxy penam-1-oxides and deri

Details Process for the preparation of 3-hydroxy penam-1-oxides and deri Process for the preparation of 3-hydroxy penam-1-oxides and deri

1974-01-16

1976-04-20

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424271, 260243C, C07D49908

Patent

active

039519562

ABSTRACT:
The invention relates to a novel process for the preparation of 3-hydroxy penam-1-oxides and esterified and etherified derivatives thereof. The process involves reaction of a penam-1-oxide mixed anhydride with a peracid followed by rearrangement and decarboxylation of the product initially formed to yield a 3-aroyloxy-penam-1-oxide. The latter compound may if desired subsequently be subjected to reductive cleavage to yield a 3-hydroxy compound, such reductive cleavage conveniently being effected by means of zinc and an ammonium salt under neutral or acidic conditions. The compounds prepared by the process of this invention are useful as intermediates in the preparation of antibiotics.

REFERENCES:
patent: 3668201 (1972-06-01), Gutowski
patent: 3668202 (1972-06-01), Foster et al.

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