6-Perhaloalkylsulfonyloxy-penicillanic acids and derivatives the

Details 6-Perhaloalkylsulfonyloxy-penicillanic acids and derivatives the 6-Perhaloalkylsulfonyloxy-penicillanic acids and derivatives the

1980-12-10

1982-10-26

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424270, C07D49900

Patent

active

043561225

ABSTRACT:
6-Alpha and 6-beta-substituted penicillanic acid derivatives of the formula: ##STR1## wherein R is H or a conventional penicillin carboxy protecting group or an ester forming residue readily hydrolyzable in vivo and R.sup.1 is a perhaloalkyl group of from 1 to 4 carbon atoms wherein the halogen atoms are fluoro or chloro, undergo SN.sub.2 nucleophilic displacement with halide or azide ions with inversion of configuration at C-6 to yield the corresponding 6-beta or 6-alpha-halo- or azido-substituted product.

REFERENCES:
patent: 4143046 (1979-03-01), Sheehan
patent: 4265882 (1981-05-01), Sheehan et al.
patent: 4282149 (1981-08-01), Sheehan et al.
Hauser et al., Helv. Chim. Acta, 50, 1327 (1967).
Sheehan et al., J. Org. Chem. 42, 2224 (1977).

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