Hydrochloric Acid → HCID 58292756, compound

Participants

Reaction Steps

To a solution of (3R)-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (1.00 g, 4.00 mmol) in THF (9 mL) was added a solution of LiOH (0.479 g, 20.0 mmol) in water (8 mL) at 0° C. The resulting mixture was stirred at room temperature for 1.5 hours then acidified to pH=2 with dilute hydrochloric acid and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (DCM/MeOH/AcOH=20:1:trace) to give pure product as a white powder after lyophilization (0.579 g, 64.9%). 1HNMR (400 MHz, DMSO-d) δ12.26 (s, 1H), 9.25 (s, 1H), 9.04 (s, 1H), 6.86 (d, J=1.95 Hz, 1H), 6.64 (d, J=1.95 Hz, 1H), 5.36 (dd, J=9.76, 2.34 Hz, 1H), 2.98 (dd, J=15.22, 2.34 Hz, 1H), 2.17 (s, 3H), 1.98 (dd, 1H). MS (ESI) m/z=221 [M−H]−.

Provenance & Evidence