Water → HCID 53234456, compound

Participants

Reaction Steps

To a solution of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (0.5 g, 1.38 mmol) in isopropanol (100 mL) was added 4 drops of concentrated sulfuric acid. The reaction was heated to reflux for 48 hrs then cooled to room temperature and added to 10 mL of water before evaporating all solvent under vacuum. The residue was partitioned between ethyl acetate and 1M HCl and the organic layer dried over Na2SO4. Removal of solvent under vacuum provided 357 mg (64%) of the title compound as a white solid. MS calcd for (C18H2O3N2O6S): 404.1. MS found (ESI negative): (M−H)−=403.1. 1H NMR (DMSO-d6) δ (ppm): 9.84 (s, 1H), 9.15 (s, 1H), 7.40-7.47 (m, 2H), 7.19 (d, J=8.4, 1H), 7.10 (d, J=2.0 Hz, 1H), 6.37 (bs, 2H), 5.91 (bs, 2H), 4.85 (m, 3H), 3.83 (s, 1H), 1.16 (d, J=6.4, 6H).

Provenance & Evidence