Sodium periodate → N-Isopropyl-N-[4-methoxyphenyl]-2-[3-methyl-2,4-dioxo-3-(2-oxo-ethyl)-5-pyridin-3-yl-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl]acetamide

Participants

Reaction Steps

To a stirring solution of 1.5 g (2.93 mmol) of 2-(3-Allyl-3-methyl-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-[4-methoxyphenyl]acetamide, prepared as in Part C, in 10 mL of dioxane and 10 mL of H2O at 0° C. is added 3.13 g (14.63 mmol, 2 equiv.) of sodium periodate followed by the addition of 2 drops of osmium tetroxide solution (4% in H2O). The resulting suspension is stirred for 4 h and then diluted with 200 mL H2O and 200 mL of EtOAc. The organic phase is washed with H2O (2×250 mL) and a solution of Na2S2O3 (10%) and then dried (MgSO4), and the solvents removed in vacuo. Purification by silica gel flash column chromatography using hexane/EtOAc 5/1 as eluent afforded 1.56 g of N-Isopropyl-N-[4-methoxyphenyl]-2-[3-methyl-2,4-dioxo-3-(2-oxo-ethyl)-5-pyridin-3-yl-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl]acetamide as an oil: 1H NMR (CDCl3, 300 MHz) δ8.51 (m, 2H), 7.68 (d, 1H, J=9), 7.39-6.93 (m, 8H), 6.71 (d, 1H, J=8), 5.78-5.64 (m, 1H), 5.08-5.00 (m, 2H), 4.72 (d, 1H, J=16), 4.39 (d, 1H, J=17), 4.08 (m, 1H), 3.85 (s, 3H), 3.81-3.79 (m, 1H), 2.11 (d, 1H, J=8), 1.77 (s, 1H), 1.60 (s, 2H), 1.21-1.07 (m, 6H); low resolution MS (FAB)m/e 513 (MH+).

Provenance & Evidence