Hydrochloric Acid → HCID 50923244, compound

Participants

Reaction Steps

To a solution of [6-(6-chloro-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.2 g, 0.55 mmol) in THF:H2O (1:1, 10 mL) at 0° C. was added a solution of LiOH (0.026 g, 1.10 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 (1 mL) at 0° C. and concentrated in vacuo. The residue was purified by preparative HPLC to give [6-(6-chloro-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.1 g, 54%). 1H NMR (400 MHz, DMSO): δ 9.21 (s, 1H), 7.96 (d, J=9.2 Hz, 1H), 7.60 (d, J=9.2 Hz, 1H), 7.30 (d, J=2.0 Hz, 1H), 7.15 (d, J=1.6 Hz, 1H), 5.52 (dd, J=2.4, 9.2 Hz, 1H), 3.10 (dd, J=2.0, 15.6 Hz, 1H), 2.31 (s, 3H), 2.18-2.12 (m, 1H). MS (ESI) m/z=333 [M−H]−.

Provenance & Evidence