Efficient synthesis of tetramethylsulfonylguanidines between a free sulfonamide group and HBTU

S Gluszok, L Goossens, P Depreux, JP Hénichart

Index: Gluszok, Sebastien; Goossens, Laurence; Depreux, Patrick; Henichart, Jean-Pierre Tetrahedron Letters, 2006 , vol. 47, # 34 p. 6087 - 6090

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Citation Number: 14

Abstract

The reaction of a sulfonamide moiety with HBTU (O-(1H-benzotriazol-1-yl)-N, N, N′, N′- tetramethyluronium hexafluorophosphate) during amide coupling, leading to the formation of tetramethylsulfonylguanidines, is described. Optimised conditions showed that HBTU was as a convenient agent for the synthesis of tetramethylsulfonylguanidines, in basic conditions. A panel of diverse sulfonamides was used to demonstrate the scope of this procedure.