Cephalosporin derivatives

US3931161A · kind A · utility

Assignee

• ALFA Farmaceutici S.p.a. · IT

Inventors

• Carlo Buitar · Bologna, IT
• Giuseppe Mascellani · Zola Predosa, IT
• Guido Guerra · Bologna, IT

Key dates

• Filing date: Mar 6, 1973
• Grant date: Jan 6, 1976
• Expiry date: Mar 6, 1993

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D501/12
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

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.