Dicyclohexylcarbodiimide → HCID 66725082, compound

Participants

Reaction Steps

Boc-alanine (0.37 mmol, 1 eq), N,N′-dicyclohexylcarbodiimide (0.47 mmol, 1.2 eq), and N-hydroxysuccinimide (0.47 mmol, 1.2 eq) were dissolved in 2 mL acetonitrile. The mixture was stirred at room temperature for 2 hr. The solid was filtered and added to (3R)-4-amino-3-[4-chloro-3-(4-pyridylmethoxy)phenyl]butanoic acid hydrochloride (68) and sodium bicarbonate (NaHCO3) (1.5 eq) in 1 mL water. The reaction was stirred at room temperature overnight. The solvent was then evaporated and treated with trifluoroacetic acid (TFA). The trifluoroacetic acid (TFA) was evaporated and purified by HPLC to provide the title compound (73). 1H-NMR (400 MHz, CD3OD): δ 8.53 (d, J=6.0 Hz, 2H), 7.57 (d, J=6.0 Hz, 2H), 7.30 (d, J=8.0 Hz, 1H), 7.05 (d, J=1.6 Hz, 1H), 6.87 (d, J=2 Hz, 1H), 5.26 (s, 2H), 3.69-3.74 (q, J=6.8 Hz, 1H), 3.56-3.61 (dd, J=8.4, 13.2 Hz, 1H), 3.28-3.39 (m, 1H), 2.55-2.61 (dd, J=16.0, 8.0 Hz, 1H), 2.44-2.50 (dd, J=15.2, 8.0 Hz, 1H), 1.23 (d, J=6.8, 3H); MS (ESI) m/z 391.87 (M+H)+.

Provenance & Evidence