Hydrochloric Acid → HCID 58292623, compound

Participants

Reaction Steps

To a solution of ethyl 2-(4-fluoro-1-hydroxy-6-isopropoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (148 mg, 0.50 mmol) in THF (2 mL) was added dropwise an solution of lithium hydroxide (102 mg, 2.5 mmol) in 3 mL of water at 0° C. The reaction mixture was stirred at room temperature for 1.5 h and then acidified to pH=2 using diluted hydrochloride acid. The reaction mixture was extracted with ethyl acetate (15 mL×2) and the 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 (24 mg, Yield: 18%). 1H NMR (400 MHz, DMSO-d) δ 12.40 (s, 1H), 9.39 (s, 1H), 7.06-7.07 (d, J=2.0 Hz, 1H), 6.87-6.91 (m, 1H), 5.51-5.54 (m, 1H), 4.62-4.64 (m, 2H), 2.90-2.95 (m, 1H), 2.31-2.33 (m, 1H), 1.28 (s, 1H). MS (ESI) m/z=536 [2M]+.

Provenance & Evidence