HCID 86753586, compound → HCID 67699881, compound

Participants

Reaction Steps

A solution of 0.23 mL of 1.0M phenylmagnesium bromide in THF is added to a solution of 0.10 g (0.21 mmol) of N-Isopropyl-2-[3-methyl-2,4-dioxo-3-(2-oxoethyl)-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide, prepared as in Intermediate 9, in 2 mL of THF at 0° C. After stirring at room temperature for 60 min the reaction is diluted with 10 mL of 1N HCl and extracted with EtOAc (×3). The organic extract is washed with sat. NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo to a colorless oil. The crude product is dissolved in 2 mL of CH2Cl2 and 0.092 g (0.42 mmol) of PCC added. After stirring at RT for 90 min, the reaction mixture is passed through a short plug of silica gel and concentrated in vacuo to a dark orange oil. Purification by silica gel flash chromatography (30% ethyl acetate/petroleum ether) gave 97 mg of the title compound as a white powder; 1H NMR (CDCl3 300 MHz) δ8.04 (d, 2H, J=7), 7.6-7.2 (m, 15H), 7.14 (t, 1H, J=7), 7.00 (d, 1H, J=7), 5.03 (m, 1H), 4.2 (m, 2H), 3.98 (dd, 1H, J=8,18), 3.61 (dd, 1H, J=5,18), 1.09 (dd, 1H, J=2,7); low resolution MS (FAB) m/e 546 (MH+).

Provenance & Evidence