PROCESS FOR THE ACYLATION OF 6-AMINOPENICILLANIC (6-APA), 7-AMINOCEPHALOSPORANIC (7-ACA) AND 7-AMINODESACETOXYCEPHALOSPORANIC (7-ADCA) ACIDS AND THEIR DERIVATIVES

摘要

ABSTRACT OF THE DISCLOSUREA process for the acylation of 6-aminopenicillanic,aminocephalosporanic, and aminodesacetoxycephalosporanic acids andtheir derivatives to prepare the corresponding penicillins andcephalosporins. The process comprises reacting in the presence ofan inert solvent a compound of the formula:(I)where R1 and R2 are hydrogen or low molecular weight alkyls, Xis an element selected from the halogen group and R is a furthergroup selected from a low molecular weight alkyl, phenyl, halogenand dimethylamin, with a carboxylic acid in the form of a tertiaryorganic base salt in methylene chloride at temperature between-15 and +20°C for a period of form 15 to 120 min, to obtain amixture of active species with a relative proportion of acid halide,N-acyl-2-oxazolidinone and 2-acyloxy-.DELTA.2-oxazoline, and furtherreacting the mixture with a solution of a compound of the formula:(II)where n may be 1 or 2, (H)2 may be 0, 2 atoms of hydrogen or a methylgroup, (H)1 is 0 or 1 atom of hydrogen, R4 an element selected from thegroup comprising hydrogen, alkali metals, trimethylsilyl, phthalidyland R3 selected from the group comprising methyl, azidomethyl,acyloxymethyl, thiolmethyl, 5-methylthiadiazolyl-2-thiomethyl, cyano-methyl, chloromethyl, and methoxymethyl.