Benzyl Bromide → HCID 53788322, compound

Participants

Reaction Conditions

Reaction Steps

An acetonitrile (1.1 mL) solution of (S)-3-[N-[3-(trifluoromethyl)benzoyl]glycyl]aminopyrrolidine (0.06 mmol) and a (piperidinomethyl)polystyrene (2.6 to 2.8 mmol/g, 30 mg) were added to an acetonitrile (0.4 mL) solution of benzyl bromide (0.050 mmol). The resulting reaction mixture was stirred at 45° C. for 5 hours. The mixture solution was cooled to room temperature, and the resin was then removed by filtration to concentrate the filtrate. The resulting residue was dissolved in acetonitrile (1.0 mL), and phenyl isocyanate (0.008 mL, 0.05 mmol) was then added to the obtained solution. The mixture solution was stirred at room temperature for 1 hour, loaded onto a Varian™ SCX column and washed with methanol (15 mL). The obtained crude product was eluted with a solution of 2 M NH3 in methanol (6 mL) and concentrated to thereby provide (S)-1-benzyl-3-[N-[3-(trifluoromethyl)benzoyl]glycyl]aminopyrrolidine (Compd. No. 239) (9.0 mg, 44%). The purity was determined by RPLC/MS (99%). ESI/MS m/e 406.0 (M++H, C21H22F3N3O2).

Provenance & Evidence