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

doi:10.1016/S0040-4039(01)90148-0

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

Medicinal Chemistry

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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 language	English (US)
Pages (from-to)	537-540
Number of pages	4
Journal	Tetrahedron Letters
Volume	22
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4039(01)90148-0
State	Published - 1981

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

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.",

author = "Moe, {Gregory R.} and Sayre, {Lawrence M.} and Portoghese, {Philip S.}",

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AU - Sayre, Lawrence M.

AU - Portoghese, Philip S.

PY - 1981

Y1 - 1981

N2 - 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.

AB - 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.

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

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