Hydrochloric Acid → HCID 58292833, compound

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Reaction Steps

To a solution of [6-(6-chloro-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.11 g, 0.30 mmol) in THF (3 mL) was added a solution of LiOH (0.036 g, 1.5 mmol) in water (1 mL) at 0° C. The resulting mixture was stirred at room temperature for 2 hours then acidified to pH 2 using 6M hydrochloric acid and extracted with EtOAc. The organic extracts were washed with water, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by preparative HPLC to give [6-(6-chloro-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid as an off white solid (0.05 g, 50%). mp 187.2-188° C. 1H NMR (400 MHz, DMSO-d δ 12.34 (s, 1H), 9.26 (s, 1H), 8.54 (s, 1H), 8.51 (s, 1H), 7.31 (s, 1H), 7.17 (s, 1H), 5.55 (m, 1H), 3.10 (dd, J=15.60, 2.80 Hz, 1H), 2.32 (s, 3H), 2.16 (m, 1H). MS (ESI) m/z: 333 (M−1)−. HPLC purity: 98.97% (Maxplot), 99.14% (220 nm).

Provenance & Evidence