PT69887A - 2-Oximino-acylamino cephem cpds. prodn. - by acylating 7-amino-cephem cpds. with complexes of 2-syn-oximino-acyl halide(s) and N,N-di:substd. amide(s) - Google Patents

Abstract

In the prodn. of cephem cpds. of formula (I) (where A is H, an equiv. of an alkali(ne earth) metal or an organic nitrogeneous base, or the residue of an ester gp.; R1 is H or opt. substd. alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, acyl, aryl, arylsulphonyl, alkylsulphonyl or heterocyclyl; R2 is furyl, thiazolyl or phenyl opt. substd. by 1-4C alkyl, aryl or opt. substd. amino; B is lower alkoxy, CH3, acetoxymethyl, carbamoylmethyl, halogen or -CH2-S-Het (Het = 5- or 6-membered ring with 1-4 hetero atoms); n is O, 1 or 2; and R1O has syn configuration), a carboxylic acid of formula (II) or a salt thereof is reacted with an acid halide-forming agent in the presence of ca 0.1-3.0 mol of a cpd. of formula (IV) (where R3, R4 and R5 are 1-6 C alkyl and R3 + R4 or R3 + R5 can also form a ring (opt. interrupted by a heteroatom), and R5 can also be di(1-6C alkyl)amino in which the alkyl gps. can be linked to form a ring which can contain an additional hetero atom), and the resulting complex is reacted with an acid of formula (III) in the form of an amine salt, an ester cleavable by acidic hydrolysis or hydroxygenolysis or a silyl ester, the carboxy gp. of the prod. opt. being converted into another gp. defined under A. (I) are obtd. in excellent yields and high purity. Rearrangement of the 2-oximino ether grouping from syn to anticonfiguration does not occur.