Penicillin and cephalosporin sulphoximines

✍ Scribed by John E.G. Kemp; Michael D. Closier; Mark H. Stefaniak

• Book ID: 104246521
• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 280 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95524-8

✦ Synopsis

Penicillin N-cyanosulphoximines v sulphilimines. Phth&midosulphoximines sulphoxides and phthalimidonitrene (from are obtained by permanganate oxidation of the are obtained from penicillin or cephalosporin N-aminophthalimide with lead tetraacetate). -We wish to report the first B-lactam sulphoximines, analoques of the novel B-lactamase inhibitor' penicillanic acid sulphone, CP-45,899 (A). PENICILLIN N-CYANOSULPHOXIMINES (Scheme 1). The penicillin sulphilimine 2 _2 (600 mq) was treated with potassium permanganate (450 mq) in acetone (20 ml) for 1 hr. at 20°, filtered through "Hyflo", and evaporated and partitioned between chloroform and water, yielding from the organic phase, sulphoximine A** (220 mg, 35%), a colourless oil, IR (CHCla) 1810 cm-l (B-lactam), 2170 cm-1 (CZNN); NMR: see Table, MS [Chemical Ionization (CHb)] P + 1 = 393, CIeH1.NbO~S requires M = 392. The aqueous layer yielded a secopenicillin, probably 4 (72 mq), a glass, IR (film) 1765 cm -' (f3-lactam), 2180 cm-l (CsN), 3440 cm-' (N-H);