An explanation for the failure of aminomethanesulfonic acid to form sulfonamides. Acyl chloride-promoted generation of α-carboxamidoalkylating electrophiles.

Gregory R. Moe, Lawrence M. Sayre, Philip S. Portoghese

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Attempted N,N-dibenzoylation of aminomethanesulfonic acid results in CS bond cleavage, generating synthetically useful α-benzamidomethylating electrophiles. The importance of this observation in regard to the reported failures to prepare sulfonamide analogs of peptides is discussed.

Original languageEnglish (US)
Pages (from-to)537-540
Number of pages4
JournalTetrahedron Letters
Volume22
Issue number6
DOIs
StatePublished - 1981

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