Triethylamine → HCID 54057429, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of (S)-α-amino-N-[2,6-bis(1-Methylethyl)phenyl]-4-(phenylmethoxy)benzenepropanamide (1.15 g, 2.67 mmol) and triethylamine (0.37 mL, 2.67 mmol) in THF (50 mL) was added tert-butylacetylchloride (0.39 mL, 2.80 mmol) dropwise. The resulting slurry was warmed to 25° C. and stirred (1 hour, 25° C.). The resulting slurry was diluted with ethyl acetate (200 mL). The organic layer was washed with 1.0N aqueous HCl (1×65 mL), with brine (1×65 mL), with saturated aqueous sodium bicarbonate (1×65 mL), with brine again (1×65 mL), then dried (MgSO4) and concentrated. The resulting oil was triturated with ether, and cooled. The resulting solid was collected by filtration, washed with cold ether, and dried in a vacuum oven at 40° C. to yield 1.2 g (85.1%) of the title compound as a white solid, melting point 209°-211.5° C.

Provenance & Evidence