Hydrochloric Acid → HCID 58292601, compound

Participants

Reaction Steps

To a solution of ethyl-2-(1,6-dihydroxy-4-methoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (133 mg, 0.50 mmol) in THF (2 mL) was added aqueous 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 hr and acidified to pH=2 using diluted hydrochloride acid. The resulting mixture was extracted with ethyl acetate (15 mL×2) and the combined organic layers were dried over anhydrous and concentrated in vacuo. The residue was purified by HPLC to give the title as a white solid (63 mg, Yield: 53%). 1H NMR (400 MHz, DMSO-d) δ 9.49 (s, 1H), 9.15 (s, 1H), 6.65 (s, 1H), 6.48 (s, 1H), 5.31-5.34 (m, 1H), 3.77 (s, 3H), 3.04-3.09 (m, 1H), 1.98-2.04 (m, 1H). MS (ESI) m/z=239 [M+H]+.

Provenance & Evidence