Isobutylamine → HCID 86616773, compound

Participants

Reaction Steps

A solution of 4-oxo-4-phenyl-2-[(trifluoroacetyl)amino]butanoic acid (3.9 g, 13.5 mmol), isobutylamine (2.68 mL, 27.0 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (5.17 g, 27.0 mmol), 1H-1,2,3-benzotriazol-1-ol hydrate (3.64 g, 27.0 mmol), and N,N-diisopropylethylamine (11.7 mL, 67.4 mmol) was stirred overnight at room temperature in dimethylformamide (20 mL). The reaction was worked up with methylene chloride and saturated sodium bicarbonate. The organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Chromatography (silica gel, 0 to 20% ethyl acetate in hexane gradient elution), gave the title compound as a yellow solid (1.41 g). MS 345 (M+1). 1H NMR (500 MHz, CDCl3) □ 7.95 (d, J=7.3 Hz, 2H), 7.92 (bs, 1H), 7.63 (t, J=7.4 Hz, 1H), 7.50 (t, J=7.7 Hz, 2H), 6.86 (bs, 1H), 5.02-4.99 (m, 1H), 3.78 (dd, J=18.3, 2.4 Hz, 1H), 3.33 (dd, J=18.3, 9.0 Hz, 1H), 3.10 (t, J=6.4 Hz, 2H), 1.81-1.73 (m, 1H), 0.88 (d, 6H).

Provenance & Evidence