Water → HCID 86753598, compound

Participants

Reaction Steps

0.12 g of 2-[2,4-dioxo-5-phenyl-3-(3-ethoxycarbonylphenyl)-carbamoyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-phenyl acetamide, prepared as in Example 1, is dissolved in 5 mL of hot ethanol. 2.5 mL of H2O and 0.13 g of K2CO3 are added and the mixture heated at reflux for 4 h and subsequently concentrated in vacuo. The residue is poured into 20 mL of 1N HCl and extracted with ethyl acetate (×3). The organic extract is washed with brine, dried over MgSO4 and concentrated in vacuo to a white solid. Purification by reverse phase C-18 MPLC (70% methanol/TFA-H2O) gave 99 mg of the title compound as a white powder: mp. 165°-170° C.; 1H NMR (CDCl3, 300 MHz) δ8.6 (s, 1H), 8.05 (s, 1H), 7.92 (d, 1H, J=7), 7.75 (d, 1H, J=7), 7.5-7.2 (m, 14H), 7.15 (t, 1H, J=7), 6.97 (d, 1H, J=7), 5.02 (m, 1H), 4.27 (s, 2H), 4.10 (t, 1H, J=7), 3.20 (d, 2H, J=7), 1.08 (d, 3H, J=7), 1.02 (d, 3H, J=7); low resolution MS (FAB) m/e 605 (MH+); Anal. (C35H32N4O6.0.5 TFA.0.5 H2O) Calc. C, 64.5; H, 5.0; N, 8.4; Found: C, 64.5; H, 5.0; N, 8.3.

Provenance & Evidence