Lithium Hydroxide → HCID 9844289, compound

Participants

Reaction Steps

1.0 N LiOH (0.57 mL, 0.57 mmol) was added dropwise at RT to a mixture of methyl (±)-7-[[[(2-benzimidazolyl)methyl]amino]carbonyl]4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (0.11 g, 0.26 mmol) in THF (4 mL) and H2O (5 mL). The resulting light brownish-yellow solution was stirred for 21.5 h, then was concentrated on the rotavap. The resulting residue was lyophilized to give the crude product (0.11 g, 100%) as a yellowish powder. Preparative HPLC. (PRP-1® column, step gradient, 10-20% CH3CN/H2O-0.1% TFA) afforded the title compound: 1H NMR (250 MHz, DMSO-d6) δ 6.45-9.06 (m, 9H), 5.53 (d, J=16 Hz, 1H), 5.13 (m, 1H), 4.86 (d, J=5 Hz, 2H), 3.87 (d, J=17 Hz, 1H), 2.95 (s, 3H), 2.80 (dd, J=17, 9 Hz, 1H), 2.57 (dd, J=17, 5 Hz, 1H); MS (ES) m/e 408.2 (M+H)+. Anal. Calcd for C21H21N5O4.4/3 CF3CO2H.H2O: C, 49.22; H, 4.25; N, 12.13. Found: C, 49.24; H, 4.22; N, 12.11.

Provenance & Evidence