Hydrochloric Acid → HCID 67252443, compound

Participants

Reaction Steps

To a solution of ethyl 2-(6-(2-(dimethylamino)ethoxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (crude) in 15 ml of THF/H2O (2/1) was added LiOH (42 mg, 1.0 mmol) in 5 ml H2O at 0° C. The reaction mixture was stirred at room temperature for 1.5 h and acidified by 1.0 N HCl to pH=6. The resulting mixture was extracted with EtOAc (3×20 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep HPLC to give the title compound as a white solid (35 mg, yield: 15%, two steps). 1H NMR (400 MHz, DMSO-d) δ9.15 (s, 1H), 7.08 (d, J=1.6 Hz, 1H), 6.89 (d, J=1.6 Hz, 1H), 5.46-5.43 (m, 1H), 4.24-4.22 (m, 2H), 4.09 (m, 1H), 3.24 (m, 2H), 3.16 (s, 3H), 3.05-3.01 (m, 1H), 2.65 (s, 6H), 2.26 (s, 3H), 2.09-2.02 (m, 1H); MS (ESI) m/z=294 [M+H]+.

Provenance & Evidence