Hydrogen chloride-ethyl acetate → N-((2S)-1-((2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)acetamide

Participants

Reaction Steps

To tert-butyl ((2S)-1-((2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamate (1.09 g) was added 4 M hydrogen chloride/ethyl acetate (10 mL), and the mixture was stirred at room temperature for 10 min, and concentrated. To the residue were added pyridine (10 mL) and acetic anhydride (10 mL), and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (640 mg). 1H NMR (300 MHz, CDCl3) δ 0.39-0.49 (2H, m), 0.63-0.75 (2H, m), 1.28-1.43 (4H, m), 2.02 (3H, s), 3.95-4.09 (4H, m), 4.36-4.50 (1H, m), 5.74 (1H, d, J=8.3 Hz), 6.95 (1H, dd, J=8.9, 2.5 Hz), 7.00 (1H, d, J=8.7 Hz), 7.11 (1H, d, J=2.3 Hz), 7.60 (1H, d, J=8.7 Hz), 8.04 (1H, dd, J=8.7, 1.9 Hz), 8.22 (1H, d, J=1.9 Hz).

Provenance & Evidence