Hydrochloric Acid → HCID 58292767, compound

Participants

Reaction Steps

To a solution of ethyl 2-(1-hydroxy-4-methoxy-6-(pyrazin-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (150 mg, 0.44 mmol) in THF (2 mL) was added an aqueous solution of lithium hydroxide (90 mg, 2.2 mmol) in 3 mL of water at 0° C., The reaction mixture was stirred at room temperature for 1.5 hr and acidified to pH=2 using diluted hydrochloride acid. The resulting mixture was extracted with ethyl acetate (15 mL×2) and combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by HPLC to give the title compound as a white solid (71 mg, Y: 51.0%). 1H NMR (400 MHz, DMSO-d) δ 9.28 (s, 1H), 8.56 (s, 1H), 8.39-8.40 (d, J=2.4 Hz, 1H), 8.24 (s, 1H), 7.00-7.02 (d, J=10.8 Hz, 2H), 5.44-5.46 (m, 1H), 3.81 (s, 3H), 3.13-3.16 (m, 1H), 2.14-2.20 (m, 1H). MS (ESI) m/z=317 [M+H]+.

Provenance & Evidence