1,2-Dichloroethane → 1-Hydroxybenzotriazole

Participants

Reaction Steps

H2O (0.54 g, 3.6 mmol) and EDC (0.686 g, 3.6 mmol) were added to a solution of methyl (±)-1-acetyl-7-carboxy-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (1.0 g, 3 mmol) in dry DMF (15 mL). After 1 h the reaction solution was added dropwise to a solution of 2,6-diaminopyridine (0.326 g, 3.0 mmol) in dry DMF (20 mL). The reaction solution was stirred for 18 h, then was concentrated. Chromatography (silica gel, 9:1 CH2Cl2/MeOH) gave the title compound (0.9 g, 70%): 1H NMR (400 MHz, DMSO-d6) δ1.80 (s, 3H), 2.3-2.7 (m, 2H), 3.0-3.1 (s, 3H), 3.5-3.6 (s, 3H), 4.1-4.2 (d, 1H), 4.7-4.8 (d, 1H), 5.7-5.9 (m, 3H), 6.2-6.3 (d, 1H), 7.3-7.5 (m, 3H), 8.0-8.1 (d, 1H), 8.2-8.3 (s, 1H); MS (ES) m/e 426.0 (M+H)+.

Provenance & Evidence