Hydrogen Peroxide → Acetate

Participants

Reaction Steps

Quinazolino[3,2-a][1,4]benzodiazepine-6(5H)-propanoic acid, 3-[[4-(aminoiminomethyl)phenyl]methoxy]-7,13-dihydro-5,13-dioxo, acetate was prepared by disolving quinazolino[3,2-a][1,4]benzodiazepine-6(5H)-propanoic acid, 3-[[4-(iminoaminomethyl)phenyl]methoxy]-7,13-dihydro-5,13-dioxo, ethyl ester (50 mgs, 0.085 mmol), in 4 mL THF and 2 mL water at room temperature and sequentally adding 0.77 mL 30% solution of hydrogen peroxide (9× excess) and 0.006 grams lithium hydroxide (0.256 mmol, 3× excess). The mixture was stirred for 2 hours, quenched with a saturated solution of sodium bisufite and 0.25 mL glacial acetic acid. The mixture was concentrated in vacuo and purified by HPLC (solvent gradient 1:4 acetonitrile:water(0.5% acetic acid) (time 0 to 10 mins.) to 3:2 acetonitrile:water(0.5% acetic acid) (time 50 mins.), 20 mL/min, C18 2" column) to yield quinazolino[3,2-a][1,4]benzodiazepine-6(5H)-propanoic acid, 3-[[4-(aminoiminomethyl)phenyl]methoxy]-7,13-dihydro-5,13-dioxo, acetate (0.005 grams, 10%).

Provenance & Evidence