Process for the acylation of 6-aminopenicillanic (6-apa),...

C - Chemistry – Metallurgy – 07 – D

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260/103, 260/113

C07D 499/12 (2006.01) C07D 499/00 (2006.01) C07D 501/06 (2006.01)

Patent

CA 1061330

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

270066

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