Ethyl bromoacetate → HCID 59656591, compound

Participants

Reaction Steps

A solution of (1S)-1-{[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]carbonyl}-2,2-dimethylpropylamine (16-1, 325 mg, 0.877 mmol, 1 equiv), ethyl bromoacetate (0.195 mL, 1.76 mmol, 2.00 equiv), and N,N-diisopropylethylamine (0.613 mL, 3.51 mmol, 4.00 equiv) in n-BuOH (4.0 mL) was heated under microwave irradiation at 150° C. for 15 minutes. The reaction mixture was concentrated and the residue was partitioned between a ethyl acetate (100 mL) and a 1:1 mixture of saturated aqueous potassium bisulfate solution and brine (100 mL). The organic layer was then washed with saturated aqueous sodium bicarbonate solution (100 mL) followed by brine (100 mL), then dried over magnesium sulfate and concentrated to give ethyl({(1S)-1-tert-butyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethyl}amino)acetate (30-1) as an off-white solid. LRMS m/z (M+H) 457.5 found, 457.2 required.

Provenance & Evidence