Hydrochloric Acid → HCID 86753597, compound

Participants

Reaction Steps

To a solution of 0.26 g (0.54 mmol) of [1-(isopropyl-phenyl-carbamoylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]acetic acid, prepared as in Intermediate 32, and 0.08 mL (0.54 mmol) of ethyl 3-aminobenzoate in 2 mL of DMF is added 0.23 g (0.54 mmol) of BOP, 72 mg (0.54 mmol) of HOBT and 63 mg (0.54 mmol) of DMAP. The black solution is stirred at RT for 21 h and subsequently poured into 20 mL of 1N HCl. The mixture is extracted with ethyl acetate (×3), washed with 1N HCl and brine, dried over MgSO4 and concentrated in vacuo. The resulting yellow oil is purified by silica gel flash chromatography (40% ethyl acetate/petroleum ether) followed by recrystallization from ethyl acetate/petroleum ether to give 0.25 g of the title compound as a white powder: mp. 187°-8° C.; 1H NMR (CDCl3, 300 MHz) δ8.01 (d, 1H, J=22), 7.77 (t, 1H, J=8), 7.5-7.2 (m, 15H), 7.12 (t, 1H, J=8), 6.94 (d, 1H, J=8), 5.02 (m, 1H), 4.36 (q, 2H, J=7), 4.26 (q, 2H, J=17), 4.04 (t, 1H, J=7), 3.10 (m, 1H), 1.39 (t, 3H, J=7), 1.08 (dd, 6H, J=4,7); low resolution MS (FAB) m/e 633 (MH+); Anal. (C37H36N4O6.0.25H2O) Calcd C, 69.7; H, 5.8; N, 8.8; Found: C, 69.6; H, 5.7; N, 8.8.

Provenance & Evidence