Potassium Carbonate → HCID 15520898, compound

Participants

Reaction Conditions

Reaction Steps

1-(Carbo-t-butoxymethyl)-4-(2-carboethoxyethyl)-7-hydroxy-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (19.5 g, 48 mmol), α-bromo-p-tolunitrile (11.3 g, 58 mmol), and potassium carbonate (9.0 g, 65 mmol) were combined in a round bottom flask. Anhydrous DMF (300 mL) was added and the reaction mixture was stirred at 40° C. for 4 days. The reaction mixture was filtered and the filtrate was concentrated in vacuo on a rotary evaporator. The residue was partitioned between ethyl acetate (500 mL) and water (100 mL). The organics were washed with saturated NaCl (50 mL) and dried over Na2SO4. The volatiles were removed in vacuo on a rotary evaporator and the residue was chromatographed on silica gel, eluting the column with 5:6 ethyl acetate/hexanes. Fractions containing pure product (Rf=0.17, 5:6 ethyl acetate/hexanes) were combined and the solvents removed in vacuo on a rotary evaporator to yield 1-(carbo-t-butoxymethyl)-4-(2-carboethoxyethyl)-7-[(4-cyanophenyl)methyl]-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (20.7 g, 83% yield).

Provenance & Evidence