Ethyl Acetate → HCID 86753586, compound

Participants

Reaction Steps

To a stirring solution of 200 mg (0.42 mmol) of 2-(3-Allyl-3-methyl-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamide, prepared as in Intermediate 6, in 10 mL of 1,4-dioxane and 3 mL of H2O is added 0.5 mL of a 4% solution of osmium tetraoxide in H2O. The resulting solution is stirred 1 min, then 220 mg (1.03 mmol, 2.5 equiv) of sodium periodate is added. The reaction mixture is stirred 3 h at RT then poured into 25 mL of EtOAc and extracted with H2O (1×25 mL), sat. NaHSO3 (1×25 mL), dried (MgSO4), and the solvents removed in vacuo. Purification of the crude material by silica gel flash column chromatography using hexane/EtOAc 1/1 as eluent afforded 141 mg of the title compound as a white foam: 1H NMR (CDCl3, 300 MHz, mixture of conformations) δ9.65 (s, 0.8H), 9.40 (s, 0.2H), 7.50-7.03 (m, 13H), 6.83 (d, 0.8H), 6.75 (d, 0.2H), 5.07 (m, 0.8H), 4.96 (m, 0.2H), 4.41 (d, 1H), 4.02 (d, 1H), 2.96 (dd, 2H), 1.62 (s, 0.6H), 1.17 (s, 2.4H), 1.09 (m, 6H); low resolution MS (FAB) m/e 619 (MH+), 574.

Provenance & Evidence