Triethylamine → HCID 15489616, compound

Participants

Reaction Steps

To a solution of 2-phenyl-4-quinoline-carboxylic acid (0.33 g, 1.3 mmol, Aldrich Chemical Company) in methylene chloride (5 mL) was added benzotriazol-1-yloxytris-(dimethyamino)phosphoniumhexafluorophosphate (BOP) (0.63 g, 1.43 mmol). The resulting mixture was shaken at room temperature for 5 min. (S)-(-)-2-arnino-3-phenyl-1-propanol (0.2 g, 1.3 mmol) was added along with triethylamine (0.2 mL, 1.43 mmol). The resulting mixture was shaken at room temperature for 24 h. Methylene chloride (10 mL) was added and the organic layer was washed with NaHCO3, H2O, brine, dried (MgSO4), filtered, and concentrated in vacuo to give an oil. The oil was purified by flash chromatography (silica gel, 30-80% EtOAc/hexane) to yield the title compound as a white solid (0.3 g, 60%). MS (ES+) m/e 383.5 [M+H]+, 405 [M+Na]+, 787 [2M+Na]+.

Provenance & Evidence