Hydrochloric Acid → HCID 58292859, compound

Participants

Reaction Conditions

Reaction Steps

An ice-cold yellow solution of (1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester G45 (0.19 g, 0.58 mmol) in MeOH (3 mL) was treated with lithium hydroxide (0.07 g, 2.92 mmol, in 2 mL of H2O) dropwise. The mixture was stirred at 0° C. for 2 h, then rt for 3 h. The mixture was acidified with 2 N HCl to pH 3, then extracted with EtOAc, dried (Na2SO4), filtered and concentrated to a yellow oil. The oil was purified by column chromatography (SiO2, AcOH/EtOAc/hexanes; 0.5:4:100) to afford 1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid (0.14 g, 83%), as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.27 (br s, 1H), 9.16 (s, 1H), 7.40 (t, J=7.42 Hz, 2H), 7.14 (t, J=7.42 Hz, 1H), 7.07 (d, J=2.35 Hz, 1H), 7.06-6.97 (m, 3H), 5.48 (dd, J=9.38, 2.34 Hz, 1H), 3.05 (dd, J=15.44, 2.74 Hz, 1H), 2.29 (s, 3H), 2.16-2.06 (m, 1H); MS (ES) m/z: 297 (M−1).

Provenance & Evidence