Methanesulfonamide → 3-Hydroxy-4-methanesulfonylamino-4-oxo-but-2-enoic acid [3-(4-fluoro-phenyl)-propyl]-methoxy-amide

Participants

Reaction Steps

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-[3-(4-fluorophenyl)-propyl]-N-methoxy-acetamide (0.300 g, 0.89 mmol) with methanesulfonamide (0.127 g, 1.33 mmol) as described in the preparation oc compound 22 gave 0.304 g (91% yield) of the title amide as a white foam after chromatography. 1H NMR (400 MHz, CDCl3) 8: mixture keto-enol forms and of rotamers equilibrating to a major enol form after a few hours in chloroform: 1.95 (2H, m, CH2), 2.6 (2H, m, CH2), 3.34, 3.35 and 3.38 (3H, 3s, SO2CH3), 3.70, 3.71 and 3.74 (3H, 3s, OCH3), 6.57 (1H, s, CH), 7.0 (2H, m, aromatics), 7.15 (2H, m, aromatics), 9.05 (1H, broad s, NH); major form after equilibration: 1.97 (2H, m, CH2), 2.64 (2H, t, CH2), 3.38 (3H, s, SO2CH3), 3.74 (3H, s, OCH3), 6.57 (1H, s, CH), 7.0 (2H, m, aromatics), 7.15 (2H, m, aromatics), 9.05 (1H, broad s, NH). MS (ESI/pos) calculated for C15H20FN2O6S, [M+H]+: 374; found: 374.

Provenance & Evidence