Hydrochloric Acid → HCID 58292679, compound

Participants

Reaction Steps

To a solution of [1-hydroxy-4-methyl-6-(pyridazin-3-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.35 g, 1.06 mmol) in THF:H2O (1:1, 6 mL) at 0° C. was added a solution of LiOH (0.076 g, 3.2 mmol) in water (1 mL). The solution was allowed to warm to room temperature over 3 hours then acidified to pH 2 with 1N HCl and extracted with EtOAc (2×10 mL). The organic extracts were washed with water (10 mL), dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (DCM:MeOH 90:10) to give [1-hydroxy-4-methyl-6-(pyridazin-3-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.15 g, 47%). 1H NMR (400 MHz, DMSO): δ 9.23 (s, 1H), 9.01 (dd, J=1.2, 4.4 Hz, 1H), 7.79-7.76 (m, 1H), 7.47 (dd, J=1.2, 9.2 Hz, 1H), 7.28 (d, J=2.0 Hz, 1H), 7.14 (d, J=2.0 Hz, 1H), 5.54 (dd, J=2.4 Hz, 1H), 3.10 (dd, J=2.4, 15.6 Hz, 1H), 2.32 (s, 3H), 2.19-2.12 (m, 1H). MS (ESI) m/z=299 [M−H]−.

Provenance & Evidence