Triethylamine → 4-Amino-2-(cyclopropanesulfonamidomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

Participants

Reaction Steps

To a stirred solution of 4-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (708 mg, 2.1 mmol) and triethylamine (1 mL, 7 mmol) in 100 mL of DCM was added cyclopropanesulfonyl chloride (0.3 g, 2.2 mmol). The reaction mixture was stirred at room temperature for 16 hours. After the majority of the solvent was removed under vacuum, the reaction mixture was extracted with ethyl acetate and washed with water, 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated, the crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the desired product as a yellow solid (45 mg, yield 5%). MS calcd for (C17H20BN3O6S2): 437.1. MS found (ESI negative): (M−H)−=336.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.04 (s, 1H), 9.17 (bs, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.50 (t, J=6.4 Hz, 1H), 7.44 (d, J=1.6 Hz, 1H), 7.22 (d, J=8.8 Hz, 1H), 7.11 (dd, J=8, 1.6 Hz, 1H), 6.83 (d, J=2.4 Hz, 1H), 6.40 (dd, J=8.4, 2.4 Hz, 1H), 4.86 (s, 2H), 4.44 (d, J=6.4 Hz, 2H), 2.60 (m, 1H), 0.92 (m, 4H).

Provenance & Evidence