p-Toluenesulfonyl isocyanate → 4-{2-[({[(4-Methylphenyl)sulfonyl]amino]carbonyl)oxy]ethyl}phenylboronic acid

Participants

Reaction Steps

4-(2-Hydroxyethyl)phenylboronic acid (1.00 g, 6.02 mmol) was treated with pyridine (90 mL) and p-toluenesulfonylisocyanate (1.01 mL, 6.63 mmol) at room temperature for 2 hours. The mixture was poured into ice-2M HCl (200 mL) and extracted with ethyl acetate, and the organic fraction was dried (MgSO4). After removal of solvent, the residue was purified flash column chromatography on silica gel eluting with dichloromethane/methanol to give 2.20 g (quant.) of the title compound as white solids: MS (ESI) m/z 381 [M+NH4]+, 362 [M−H]−, 1H-NMR (DMSO-d6) δ 2.40 (3H, s), 2.81 (2H, t, J=6.6 Hz), 4.18 (2H, t, J=6.6 Hz), 7.13 (2H, d, J=7.7 Hz), 7.40 (2H, d, J=8.6 Hz), 7.67-7.75 (2H, m), 7.97 (1H, s), 11.95 (1H, br).

Provenance & Evidence