Synthetic scheme for the new compounds prepared
in this study. (a) Ethyl 4-chloroacetoacetate,
H2SO4, rt, 6 d; (b) Br2,
AcOH, rt, 1h; (c) DBU, AcOH, benzene, reflux, 1.5 h;
(d) DBU,
N-(tert-butoxycarbonyl)-α-tert-butyl
glutamate, benzene, reflux, 1 h; (e)
CF3CO2H, CH2Cl2, rt, 1
d; (f) H2O, reflux, 14 h; (g)
i. DMAP, 4-nitrophenyl chloroformate, CH3CN, rt,
7 h. ii DMAP, di-tert-butyl glutamate
hydrochloric acid salt, rt, 23 h; (h)
CF3CO2H, CH2Cl2, rt, 2
d.