Pfizer Corporation

Donald K Pirie

Robert A Volkmann

Edward F Kleinman

Paul D Weeks

Berkeley W Cue

A process for production of a 2-azetidinone-1-oxoacetate of the formula ##STR1## useful as an intermediate for preparation of 2-SR.sup.2 -substituted-2-penem-3-carboxylate andtibacterial agents; R is a conventional hydroxy protecting group, R.sup.1 is certain carboxy protecting groups and ##STR2## and m and n are each 0, 1 or 2; which comprises contacting a corresponding (2-oxo-1-axetidinyl)-N-2-hydroxyacetate ester of the formula ##STR3## with manganese dioxide.

Method for preparation of azetidinone-1-oxoacetate by oxidation of the

6-alpha/beta-[(C.sub.1 -C.sub.4)Alkoxyaminomethyl and benzyloxyaminomethyl]penicillanic acid 1,1-dioxides, pharmaceutically acceptable salts thereof and conventional esters thereof hydrolyzable under physiological conditions, all of which are useful in medicine as beta-lactamase inhibitors; intermediates and processes therefor; and a process for the conversion of the present compounds to 6-alpha- and 6-beta-(aminomethyl)penicillanic acid 1,1-dioxides and derivatives.

Process for preparing penicillanic acid 1,1-dioxide derivatives

Beta-lactamase inhibiting 6-(alkoxyamino-methyl) penicillanic acid

A process for the debromination of 6-monobromo- and 6,6-dibromopenicillanic acid, and various derivatives thereof, by the action of a bisulfite salt. The debrominated compounds produced find various utilities, as beta-lactamase inhibitors useful in therapy in combination with known beta-lactam antibiotics, or as intermediates in the further synthesis of useful beta-lactam compounds.

Process for debromination of dibromopenicillanic acid and derivatives

Bis-esters of resorcinol (1,3-dihydroxybenzene) with ampicillin or amoxicillin and penicillanic acid 1,1-dioxide or 6-beta-(hydroxymethyl)penicillanic acid 1,1-dioxide, having utility as antibacterial agents; processes therefor; and intermediates therefor, including m-hydroxyphenyl esters of penicillanic acid, 6-beta-(hydroxymethyl)penicillanic acid, and azidocillin.

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Uncasville, CT, United States of America

Donald K Pirie