Methanol → HCID 53695482, compound

Participants

Reaction Steps

To a solution of N1-[[1-(benzyloxycarbonylamino(benzyloxycarbonylimino)methyl)piperidin-3-yl]carbonyl]-N2-(4-t-butylbenzoyl)-4-methoxycarbonyl-1,2-benzenediamine (0.7 g, 0.94 mmol), CH3OH (10 mL), dioxane (10 mL), and water (6 mL) was added 1 N NaOH (3.7 mL, 3.7 mmol). The reaction was stirred for 48 h and was concentrated. The residue was partitioned between H2O (100 mL) and Et2O (100 mL). The aqueous layer was extracted with Et2O (100 mL), acidified to pH 2.5 with 5 N HCl and extracted with EtOAc (3×200 mL). The combined EtOAc layers were washed with water, MgSO4 dried, concentrated and crystallized at 0° C. overnight to give the title compound as a solid (0.63 g, 92%); TLC: Rf=0.38 (1:15: 135 acetic acid:methanol:chloroform); NMR (CDCl3) δ1.35 (s,9H), 1.50-2.05 (m, 8H), 3.20-3.40 (m, 1N), 3.60-4.05 (m, 3H), 5.05 (s, 4H), 7.20-7.35 (m, 12H), 7.40-7.50 (m, 2H), 7.55-7.65 (m, 1H), 7.90-8.00 (m, 2H), 8.05-8.15 (m, 1H); MS(FAB): 734 (MH+).

Provenance & Evidence