HCID 67254070, compound → HCID 58292855, compound

Participants

Reaction Steps

A solution of [6-(3-benzyloxy-phenoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.55 g, 1.36 mmol) and 10% Pd/C (0.4 g) in EtOH (100 mL) was hydrogenated at 40 psi for 30 minutes. The mixture was filtered through a pad of celite and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (MeOH:DCM 10:90) to give [1-hydroxy-6-(3-hydroxy-phenoxy)-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.25 g, 58%). mp 138.2-140.1° C. 1H NMR (400 MHz, DMSO): δ 12.34 (s, 1H), 9.59 (s, 1H), 9.19 (s, 1H), 7.15 (t, J=8.0 Hz, 1H), 7.09 (d, J=2.0 Hz, 1H), 6.98 (d, J=1.6 Hz, 1H), 6.53 (dd, J=8.4, 2.0 Hz, 1H), 6.42 (dd, J=8.0, 2.0 Hz, 1H), 6.35 (t, J=2.4 Hz, 1H), 5.48 (dd, J=9.2, 2.4 Hz, 1H), 3.09 (dd, J=15.2, 2.4 Hz, 1H), 2.28 (s, 3H), 2.14-2.07 (m, 1H). MS (ESI) m/z: 315 (M+1)+. HPLC purity: 98.56% (Maxplot), 98.87% (220 nm).

Provenance & Evidence