4-Methylmorpholine → HCID 25221636, compound

Participants

Reaction Steps

To a stirred mixture of 30 mg (0.08 mmol) of 1, 11 mg (0.08 mmol) of N-hydroxybenzotriazole (HOBt), 21 mg (0.11 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI.HCl), and 28 mL (0.25 mmol) of 4-methylmorpholine in 5 mL dry CH2Cl2 was added 6 mg (0.08 mmol) of HONH2.HCl at room temperature. The resulting mixture was stirred overnight and washed with 5 mL of H2O. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc) to give 6 mg (20%) of 2 as a white viscous residue that solidified slowly at room temperature: 1H NMR (400 MHz, DMSO-d6) δ 10.69 (s, 1H), 8.90 (brs, 1H), 7.86 (d, J=8.6 Hz, 2H), 7.72 (s, 1H), 7.68-7.50 (m, 7H), 3.39 (s, 2H); 13C NMR (100 MHz, DMSO-d6) 185.9, 166.3, 148.8, 139.7, 138.6, 137.4, 136.0, 133.0, 132.3, 130.6, 129.2, 129.2, 129.1, 128.9; IR (KBr) cm−1 3305, 3223, 3060, 2921, 1746, 1631, 1436; LREIMS C19H14ClNO3S requires 371.04. Found: 371 ([M+], 9%), 355 (100%).

Provenance & Evidence