Collect. Czech. Chem. Commun. 1989, 54, 1734-1745

New synthesis of oxime-type beta-lactam antibiotics

Martin Mandel, Ludvík Novák, Miroslav Rajšner, Jiří Holubek and Vladislava Holá

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


Reaction of anhydrous acids II with phosphorus pentachloride afforded hydrochlorides of chlorides III which were used in acylations of N,O-bis(trimethylsilyl) derivatives of 6-aminopenicillanic and 7-aminodeacetoxycephalosporanic acid. Change of the (Z)-configuration of the alkoxyimino group during the synthesis was observed only in the methoxyimino series. The prepared penicillins IV are effective against gram-positive as well as gram-negative bacteria.