Lithium Hydroxide → HCID 18418862, compound

Participants

Reaction Steps

1.0 N LiOH (1.1 mL, 1.1 mmol) was added dropwise to a mixture of methyl (±)-7-[[(6-amino-3-pyridinyl)amino]carbonyl]-3-oxo-4-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (0.23 g, 0.48 mmol) in THF (12 mL) and H2O (17 mL) at RT. After 22.5 h, the dark reddish-brown reaction mixture was concentrated on the rotavap to remove excess THF. The resulting reddish solution was cooled in an ice-bath, and neutralized with 1.0 N AcOH (1.8 mL). The precipitate was collected by suction filtration, washed with water and ether, and air-dried to give the title compound (0.19 g, 86%) as a pinkish-purple solid: 1H NMR (400 MHz, DMSO-d6) δ9.55 (s, 1H), 6.40-8.29 (m, 7H), 5.69 (s, 2H), 5.42 (d, J=17 Hz, 1H), 5.09 (br, 1H), 3.95 (dd, J=17,1H), 3.59-3.65 (m, 2H), 2.51-2.82 (m, 4H); MS (ES) m/e 460.2 (M+H)+. Anal. Calcd for C25H25N5O4.9/4 H2O: C, 60.05; H, 5.98; N, 14.01. Found: C, 59.79; H, 5.92; N, 13.64.

Provenance & Evidence