Hydrochloric Acid → HCID 67254070, compound

Participants

Reaction Steps

To a solution of [6-(3-benzyloxy-phenoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (1.0 g, 2.3 mmol) in THF (20 mL) at 0° C. was added a solution of LiOH (0.278 g, 11.5 mmol) in water (10 mL). The solution was allowed to warm to room temperature and stirred for 3 hours then acidified to pH 2 with 6M HCl. The solution was extracted with ethyl acetate (2×50 mL) and the organic extracts washed with water, brine, dried over sodium sulfate and concentrated in vacuo to give [6-(3-benzyloxy-phenoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid as a clear oil (0.85 g, 91%) which was used without further purification. 1H NMR (400 MHz, DMSO): δ 9.13 (s, 1H), 7.42-7.25 (m, 6H), 7.08 (s, 1H), 6.96 (s, 1H), 6.79 (dd, J=8.4, 2.0 Hz, 1H), 6.64 (s, 1H), 6.51 (d, J=6.8 Hz, 1H), 5.48 (d, J=7.6 Hz, 1H), 5.07 (s, 2H), 3.10 (dd, J=15.6, 2.4 Hz, 1H), 2.26 (s, 3H), 2.13-2.07 (m, 1H).

Provenance & Evidence