Sodium Hydroxide → HCID 21830389, compound

Participants

Reaction Steps

1.0 N NaOH (1 mL, 1.0 mmol) was added dropwise to a solution of methyl (±)-7-[[[(2-indolyl)methyl]amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (0.35 g, 0.83 mmol) in THF (5 mL) and MeOH (2 mL) at RT. The resulting mixture was stirred for 20 h then was concentrated. The residue was dissolved in H2O (20 mL) and acidified with TFA. ODS chromatography (27% CH3CN/H2O-0.1% TFA), concentration and lyophilization gave the title compound (100 mg, 30%) as an off-white solid: HPLC (ODS, 5-60% CH3CN/H2O-0. 1% TFA gradient elution over 20 min) K'=10.2; 1H NMR (400 MHz, DMSO-d6) δ 8.55 (t, 1H), 7.57 (s, 1H), 7.56 (d, 1H), 7.43 (d, 1H), 7.33 (d, 1H), 7.01 (t, 1H), 6.93 (t, 1H), 6.55 (d, 1H), 6.33 (br, 1H), 6.25 (s, 1H), 5.49 (d, 1H), 5.08 (t, 1H), 4.55 (d, 2H), 3.82 (d, 1H), 2.92 (s, 3H), 2.75 (dd, 1H), 2.53 (d, 1H); MS (ES) m/e 407.2(M+H)+. Anal. Calcd for C22H22N4O4.H2O: C, 62.25; H, 5.70; N, 13.20. Found: C, 62.66; H, 5.64; N, 12.99.

Provenance & Evidence