Hydrochloric Acid → HCID 58292719, compound

Participants

Reaction Steps

To a solution of [1-hydroxy-4-methyl-6-(pyrimidin-4-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.4 g, 1.21 mmol) in THF:H2O (1:1, 10 mL) at 0° C. was added LiOH (0.087 g, 3.65 mmol) in water (1 mL). The solution was allowed to warm to room temperature over 6 hours then acidified to pH 2 with 1N HCl at 0° C. and extracted with EtOAc (2×10 mL). The organic extracts were dried and concentrated in vacuo. The residue was purified by preparative HPLC to give [1-hydroxy-4-methyl-6-(pyrimidin-4-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.3 g, 82%). 1H NMR (400 MHz, DMSO): δ 9.25 (s, 1H), 8.73 (s, 1H), 8.65 (d, J=5.6 Hz, 1H), 7.26 (d, J=2.0 Hz, 1H), 7.12 (d, J=7.2 Hz, 2H), 5.51 (dd, J=2.4, 9.6 Hz, 1H), 3.07 (dd, J=2.0, 15.2 Hz, 1H), 2.29 (s, 3H), 2.17-2.11 (m, 1H). MS (ESI) m/z=301 [M+H]+.

Provenance & Evidence