Alfa Farmaceutici S.p.a.

Guido Guerra

Giuseppe Mascellani

Carlo Buitar

Renato Andrisano

A process for the recovery of cephalosporin C from an aqueous medium, including the steps of treating the medium with a sulphonyl chloride of formula R--SO.sub.2 Cl, in which R is a substituted or unsubstituted alkyl group having from 4 to 10 carbon atoms, or a substituted or unsubstituted aryl group, to convert the cephalosporin C to the corresponding sulphonamide and extracting the sulphonamide with an essentially water immiscible solvent. The sulphonyl chloride may be toluene-p-sulphonyl chloride, p-isopropylbenzenesulphonyl chloride or .beta.-naphthalenesulphonyl chloride. The molar ratio of sulphonyl chloride to cephalosporin C present in the aqueous medium is from 3 to 10. The temperature of the reaction of sulphonyl chloride with cephalosporin C is maintained in the range from 10.degree. to 20.degree. C. The water immiscible solvent is selected from ethyl acetate, n-butanol and methylisobutylketone. The pH of the reaction medium is maintained at a value of from 7.5 to 9.5 by means of a buffering agent. The extraction of the sulphonamide of cephalosporin C is carried out at a pH of from 1 to 4.

Process for the recovery of cephalosporin C and derivatives thereof

Novel cephalosporin derivatives, for example N-acetoacetylcephalosporin C, N-decanoylcephalosporin C, N-dodecanoylcephalosporin C and N-hendecenoylcephalosporin C, are useful as readily-recoverable intermediates in the isolation of cephalosporin C value from fermentation broths and in the preparation of 7-aminocephalosporanic acid. They are prepared by treating an aqueous solution containing cephalosporin C, such as a fermentation broth, with diketene or an acid chloride such as decanoyl chloride, dodecanoyl chloride or hendecenoyl chloride, followed by solvent extraction. They are converted into 7-aminocephalosporanic acid by successively forming the silyl di-ester, halogenating to the imino-halide, converting the imino-ether and hydrolysing to 7-ACA.

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Bologna, Italy

Guido Guerra