Silver acetate-assisted formation of amides from acyl chlorides

[Display omitted] •We developed a mild and high-yielding method for the amide bond formation.•The use of silver acetate assists the acylation of amines by acyl chlorides.•Amides are isolated without chromatography; optical configurations are maintained.•N-Nosyl-amino acid chlorides are easily transf...

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Veröffentlicht in:Tetrahedron letters 2015-01, Vol.56 (1), p.199-202
Hauptverfasser: Leggio, A., Belsito, E.L., Di Gioia, M.L., Leotta, V., Romio, E., Siciliano, C., Liguori, A.
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Sprache:eng
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Zusammenfassung:[Display omitted] •We developed a mild and high-yielding method for the amide bond formation.•The use of silver acetate assists the acylation of amines by acyl chlorides.•Amides are isolated without chromatography; optical configurations are maintained.•N-Nosyl-amino acid chlorides are easily transformed into amides and dipeptides.•Peptide bonds are created also using N-methyl-N-nosyl-amino acid chlorides. A mild method for the aminolysis of carboxylic acid chlorides to give amides is disclosed. Reactions are carried out in the presence of silver acetate in non-aqueous environments under heterogeneous phase conditions. Amides are easily recovered in very good to excellent yields and without racemization. The approach is successful in forming peptide bonds starting from N-(4-nitrobenzenesulfonyl)-amino acid chlorides and allows the formation of dipeptides also when N-methylated amino acid derivatives are used.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.11.067