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Ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o-NosylOXY): A Recyclable Coupling Reagent for Racemization free Synthesis of Peptide, Amide, Hydroxamate and Ester

D Dev , NB Palakurthy , K Thalluri , J Chandra , B Mandal, J. Org. Chem., Just Accepted Manuscript, Publication Date (Web): May 21, 2014

Ubiquitousness of amide and ester functionality makes coupling reactions extremely important. Although numerous coupling reagents are available, methods of preparation of the common and efficient reagents are cumbersome. Those reagents generate substantial amount of chemical waste and lack recyclability. Ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o-NosylOXY), the first member of a new generation of coupling reagents, is found for which byproducts can be easily recovered and reused for the synthesis of the same reagent making the method more environment friendly and cost effective. Synthesis of amides, hydroxamates, peptides, and esters using this reagent is described. Synthesis of the difficult sequences, for example, islet amyloid polypeptide (22-27) fragment (with a C-terminal Gly, H-Asn-Phe-Gly-Ala-Ile-Leu-Gly-NH2) and acyl carrier protein (65-74) fragment (H-Val-Gln-Ala-Ala-Ile-Asp-Tyr-Ile-Asn-Gly-OH), following solid phase peptide synthesis (SPPS) protocol and Amyloid β (39-42) peptide (Boc-Val-Val-IIe-Ala-OMe) following solution phase strategy is demonstrated. The remarkable improvement is noticed with respect to reaction time, yield, and retention of stereochemistry. A mechanistic investigation and recyclability are also described.

Copyright © 2014 American Chemical Society