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 |
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Hauptverfasser: | , , , , , , |
Format: | Artikel |
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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2014.11.067 |