Sec-Butylamine → HCID 53234533, compound

Participants

Reaction Steps

To a stirred solution of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (720 mg, 2 mmol) and sec-butylamine (0.7 mL, 7 mmol) in 20 mL of DMF was added PyBOP (1550 mg, 3 mmol) and TEA (3 mL, 15 mmol). The reaction mixture was stirred for 16 hours. After water was added, 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 first purified by preparative HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) followed by ISCO CombiFlash Rf silica chromatography eluted with 88:10:2 chloroform:MeOH:H2O to give the desired product as a yellow solid (100 mg, yield 13%). MS calcd for (C19H24BN3O5S): 417.2. MS found (ESI negative): (M−H)−=416.4. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.90 (s, 1H), 9.17 (s, 1H), 7.84 (d, J=8 Hz, 1H), 7.44 (d, J=2 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 7.22 (d, J=8 Hz, 1H), 7.10 (dd, J=8.4, 2 Hz, 1H), 6.48 (d, J=2.4 Hz, 1H), 6.34 (dd, J=8.8, 2.4 Hz, 1H), 5.93 (bs, 2H), 4.87 (s, 2H), 3.78 (s, 2H), 3.71 (m, 1H), 1.40 (m, 2H), 1.05 (d, J=6.4 Hz, 3H), 0.82 (t, J=7.2 Hz, 3H).

Provenance & Evidence