Fl. Wagenaar et Jf. Kerwin, METHODOLOGY FOR THE PREPARATION OF N-GUANIDINO-MODIFIED ARGININES ANDRELATED DERIVATIVES, Journal of organic chemistry, 58(16), 1993, pp. 4331-4338
Methods for the preparation of N(G)-modified arginines and N(delta)-he
terocyclic ornithines are described. The reactive cyanamide intermedia
te tert-butyl N(alpha)-Boc-N(delta)-cyano-L-ornithinate (2). prepared
either by treatment of tert-butyl N(alpha)-BOC-L-ornithinate (5) with
cyanogen bromide or by dehydration of tert-butyl N(alpha)-Boc-L-citrul
linate (6), was utilized to prepare N(G)-hydroxy-L-arginine, N(G)-amin
o-L-arginine, and N(G)-methoxy-L-arginine. Intermediates 3a and 3b, de
rived from treatment of 5 with diphenyl cyanocarbonimidate (19), react
ed with nitrogen nucleophiles to produce novel N(G)-cyano-L-arginine a
nd N(delta)-heterocyclic L-ornithine analogs.