Dienstag, 19. Oktober 2021 | 14:00 - 14:30

Forum

Programmpunkt

«Self-Regeneration of Stereocenters in Flow»

Roger Marti, Lara Amini-Rentsch, Sandrine Aeby, Vincent Pilloud, Daniel Meyer University of Applied Sciences Western Switzerland (HES-SO), Haute Ecole d’Ing nierie et d’Architecture de Fribourg, Institute ChemTech, Boulevard de Pérolles 80, CH-1700 Fribourg, roger.marti@hefr.ch

Natural as well as unnatural, modified amino acids play central role as important building blocks in medicinal chemistry and drug development. Alkenyl amino acid building blocks, such as Fmoc-S-2-(4’-pentenyl)-alanine or Fmoc-R-2-(7’-octenyl)-alanine are among others required for the synthesis of hydrocarbon-stapled peptides. This modification stabilizes the helical structure of short peptides and so increase the affinity to the target [1]. Such alkenyl amino acids can be prepared by the elegant concept of self-regeneration of stereocenters introduced by Seebach [2, 3].

Here, we present our work, which is on the evaluation and optimization of the alkylation of oxazolidinones in flow regarding selectivity and yield. We will compare and critical discuss the reactions between batch and flow conditions.

 

[1] L. D. Walensky, G. H. Bird, J. Med. Chem. 2014, 57, 6275–6288.

[2] Long et al., J. Med. Chem. 2013, 56, 5601−5612.

[3] D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. Int. Ed. 1996, 35, 2708-2748.

 

 

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