Development of a Practical and Convergent Process for the Preparation of Sulopenem

Previous synthetic processes for the preparation of sulopenem involved multistep linear sequences in which the chiral sulfoxide side chain was introduced early in the process. This contribution summarizes the development of a practical and convergent process for the large-scale preparation of 1. The...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic process research & development 2012-08, Vol.16 (8), p.1348-1359
Hauptverfasser: Brenek, Steven J, Caron, Stéphane, Chisowa, Esmort, Delude, Mark P, Drexler, Michele T, Ewing, Marcus D, Handfield, Robert E, Ide, Nathan D, Nadkarni, Durgesh V, Nelson, Jade D, Olivier, Mark, Perfect, Hahdi H, Phillips, James E, Teixeira, John J, Weekly, R. Matt, Zelina, John P
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Previous synthetic processes for the preparation of sulopenem involved multistep linear sequences in which the chiral sulfoxide side chain was introduced early in the process. This contribution summarizes the development of a practical and convergent process for the large-scale preparation of 1. The key step in the synthesis involves cyclization of an oxalimide intermediate to provide the thiopenem core. This convergent strategy allows for late introduction of the expensive and labile chiral sulfoxide subunit. Additionally, a regioselective sulfur oxidation and an improved deprotection sequence were developed. The latter provides API of high purity without the need for recrystallization.
ISSN:1083-6160
1520-586X
DOI:10.1021/op300131e