Chemistry of Cephalosporin Antibiotics. X.¹ Synthesis of Methyl 3-Formyl-7-(thiophene-2-acetamido)-3-cephem-4-carboxylate, a New Cephalosporin Derivative

Ceftibuten: Development of a Commercial Process Based on Cephalosporin C. Part II. Process for the Manufacture of 3-Exomethylene-7(R)-glutaroylaminocepham-4-carboxylic Acid 1(S)-Oxide

“…After reviewing this literature, and determining the fermentation/extraction and chemical processing changes which would be required to commercialize a process scheme based on intermediate 6 or 8 we were dissuaded from pursuing such a route. In brief, as is the case in utilizing 4 and 5 , evaluation of the published chemical methods for converting 3-substituted cephalosporins to the desired 3-H cephalosporins from a cost standpoint revealed that we would need to undertake a great deal of exploratory work to even be in a position to determine which of the many raw chemical recipes from this research literature 10 might be improved, integrated, and developed to create an economically attractive process. In addition our evaluation indicated that a relatively large investment in new process equipment would be needed.…”

Neue β‐Lactam‐Antibiotika. Über die Darstellung und Decarbonylierung von 3‐Formylcephem‐Verbindungen. Modifikationen von Antibiotica, 12. Mitteilung [1]

“…C 69,40 H 4.99 N 5.78 0 13,21 S 6,62% (484,57) Gef. ,, 69,47 ,,5,Ol ,,5,73 ,,13,26 ,,6,66% (C,H5)21; 7530 (s/3 CeH5).…”

“…Die vcrsuchsweise Konfigurationszuordnung an C(4) bei 10a beruht auf Analogic [5]. Diese Tatsache ist beincrkenswcrt, da das d z :d3-Gleichgewicht bei Cephem-4-carbonslureestern in den nicisten uns bishcr bekannten Fallen eher auf Seiten des da-Isomeren licgt.…”

“…Gef. ,, 56,58 ,,5,31 ,,9,46 ,,21,36 ,,. -a) Oxydation mit 2, Eine Losung von 0,900 g (2,58 mmol) 3-Hydroxymethyl-7~-phenylacrtamidoceph-2-em-4a-carbonsaure (3a) [l] in 50 ml abs.…”