Tetrahedron p. 11235 - 11250 (1995)
Update date:2022-08-03
Topics:
Rijkers, Dirk T. S.
Adams, Hans P. H. M.
Hemker, H. Coenraad
Tesser, Godefridus I.
A method is described for the synthesis of N(α)-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) N(α)-protective functions or allyl-derived protections, but also with N(α)-trityl amino acids, albeit in lower yield. The reaction runs in pyridine and its mechanism implies carboxyl activation by formation of a mixed anhydride with phosphorodichloridic acid (HOPOCl2).
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