Aziridine → HCID 9863629, compound

Participants

Reaction Steps

A solution of the above benzamide (0.84 g, 2.38 mmol) and aziridine (0 74 mL, 14 3 mmol) in EtOAc (20 mL) was stirred at room temperature for 16 h. The reaction mixture was worked up and the residue was chromatographed on silica gel, eluting with EtOAc/MeOH (4:1) to give 10 (0.65 g, 76%), mp (EtOAc) 120-123° C. 1H NMR [(CD3)2SO] δ8.71 (t, J=5.8 Hz, 1H, NH), 8.45 (s, 1H, H-3), 744 (s, 1H, H-6), 477 (d, J=5 0 Hz, 1H, CHOH), 4.54 (t, J=5 8 Hz, 1H, CH2OH), 3.70-361 (m, 1H, CHOH), 3.45-3.36 (m, 3H, CH2OH, CONHCHH), 3 41 (s, 3H, CH3), 3.17-3.07 (m, 1H, CONHCHH), 2.47 (s, 4H, aziridine-H). Anal. Calcd for C13H17N3O7S.0.5H2O: C, 42.39,H, 4.93; N, 11.41. Found C, 41.98; H, 5.11, N, 10.97%.

Provenance & Evidence