Adams, Hans P.H.M.

Hemker, H. Coenraad

Rijkers, Dirk R.S.

Tesser, Godefridus I.

English

A method is described for the synthesis of N-alpha-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(a)lpha-protective functions or allyl-derived protections, but also with N-alpha-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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A convenient synthesis of amino acid p-nitroanilides:Synthons in the synthesis of protease substrates

https://cris.maastrichtuniversity.nl/files/46987098/ae043d16-f863-4488-ab57-95fbecaa9b2a.pdf

A convenient synthesis of amino acid p-nitroanilides:Synthons in the synthesis of protease substrates

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