Hydrochloric Acid → HCID 67254107, compound

Participants

Reaction Steps

To a solution of ethyl 2-(6-(2-(tert-butoxycarbonyl)ethoxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (80 mg, 0.2 mmol) in 16 mL of THF/H2O (1/1) was added LiOH (42 mg, 1.0 mmol) in 5 mL of H2O at 0° C. The reaction mixture was stirred at room temperature for 1.5 h and acidified by 1 N HCl to pH=5. The resulting mixture was extracted with EtOAc (3×20 ml). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified by prep HPLC to give the title compound as an off-white powder (60 mg, yield: 82.2%). 1H NMR (400 MHz, DMSO) δ12.23 (s, 1H), 9.09 (s, 1H), 7.03 (d, J=2.0 Hz, 1H), 7.01-6.98 (m, 1H), 6.85 (d, J=2.0 Hz, 1H), 5.45-5.42 (m, 1H), 3.96-3.93 (m, 2H), 3.27-3.31 (m, 2H), 3.00-3.04 (m, 1H), 2.25 (s, 3H), 2.08-2.02 (m, 1H), 1.39 (s, 9H); MS (ESI) m/z=366 [M+H]+.

Provenance & Evidence