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Syntheses of a series of imidazolin-2-one dipeptides 175–177 (for R' and R'' see text). Reagents and conditions: a) H2NCHR'C(O)NHCHR''COOMe, MgSO4, CH2Cl2, rt, 5 h; b) NaBH3CN, MeOH, rt, overnight; c, triphosgene, NaH, THF, −10 °C, 2 h; d) MsOH, anisole, hexane, reflux, 4 h; e) NaN3, DMF, 80 °C, overnight; f) H2, Pd/C, MeOH, rt, overnight; g) PhNCO, THF, rt, 3 h or phenyl (pyrimidin-2-yl)carbamate, MeCN, reflux, 3 h or PhSO2Cl, TEA, THF, reflux, 1 h; h) NaOH 1N, MeOH/H2O, rt, 1 h.
