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DOI: 10.1055/s-0034-1379917
Efficient Synthesis of Nicotinic Acid Based Pseudopeptides Bearing an Amidoxime Function
Publikationsverlauf
Received: 02. Februar 2015
Accepted after revision: 27. März 2015
Publikationsdatum:
19. Mai 2015 (online)
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Abstract
The synthesis of nicotinic acid based amino acid units bearing an amidoxime function on the pyridine ring has been developed. The starting 2-cyanonicotinic acid was efficiently coupled with methyl esters of l-α-amino acids to afford intermediate 2-cyanopyridin-3-yl-containing pseudopeptides together with the tautomeric methyl esters of (2S)-2-(7-imino-5-oxo-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)alkanoic acids. Regioselective pyrrolidine ring opening of these esters occurred upon hydroxylamine hydrochloride treatment, giving rise to the open-chain pyridin-3-yl 2-amidoxime pseudopeptides bearing the same structure as amidoximes obtained by direct hydroxyamination of the corresponding cyano esters.
Key words
amino acids - coupling - ring opening - amidoximes - pyridines - pseudopeptides - prodrugsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379917.
- Supporting Information
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