TY - JOUR
T1 - A convenient synthesis of amino acid p-nitroanilides
T2 - Synthons in the synthesis of protease substrates
AU - Rijkers, Dirk R.S.
AU - Adams, Hans P.H.M.
AU - Hemker, H. Coenraad
AU - Tesser, Godefridus I.
PY - 1995/10/9
Y1 - 1995/10/9
N2 - 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).
AB - 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).
U2 - 10.1016/0040-4020(95)00671-T
DO - 10.1016/0040-4020(95)00671-T
M3 - Article
SN - 0040-4020
VL - 51
SP - 11235
EP - 11250
JO - Tetrahedron
JF - Tetrahedron
IS - 41
ER -