Sodium hydride → tert-Butyl 3-{3-[(cyclopentyl{4-[(4-oxoquinazolin-3(4H)-yl)methyl]phenyl}acetyl)amino]-2-methylphenyl}propanoate

Participants

Reaction Conditions

Reaction Steps

15 mg (0.39 mmol, content 60%) of sodium hydride were added to a solution of 34 mg (0.23 mmol) of quinazolin-4(3H)-one in 5 ml of DMF, and the mixture was stirred under an atmosphere of argon at 0° C. for 30 min. 100 mg (0.19 mmol) of tert-butyl 3-[3-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate, dissolved in 1 ml of DMF, were then added to the reaction solution, and the latter was slowly warmed to toom temperature. After the reaction had gone to completion (monitored by TLC; cyclohexane/ethyl acetate 2:1), 1 ml of saturated ammonium chloride solution was added and the reaction mixture was purified directly by preparative HPLC. This gave 28 mg (0.05 mmol, 25% of theory) of the racemic title compound.

Provenance & Evidence