A convenient synthesis of amino acid p-nitroanilides; synthons in the synthesis of protease substrates

DTS Rijkers, HPHM Adams, HC Hemker, GI Tesser

Index: Rijkers, Dirk T. S.; Adams, Hans P. H. M.; Hemker, H. Coenraad; Tesser, Godefridus I. Tetrahedron, 1995 , vol. 51, # 41 p. 11235 - 11250

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Citation Number: 49

Abstract

A method is described for the synthesis of Nα-protected bi-and trifunctional amino acid p- nitroanilides. The reaction uses phosphorus oxychloride as the condensing agent. The synthesis is simple, rapid, free of racemization and affords yields between 70–90%. The synthesis can be performed not only with amino acid derivatives of the urethane type including acid-labile (Z. Boc) and base-labile (Fmoc, Msc) Nα-proteclivc functions or allyl- ...