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

HRID 2181143Notes

Reaction equation

HRID 2181143 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[O:11][CH3:12])=[O:9])[C:4](=O)[O:3]1.[CH3:25][S:26]([NH2:29])(=[O:28])=[O:27]>>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH2:13][N:10]([O:11][CH3:12])[C:8](=[O:9])[CH:7]=[C:5]([OH:6])[C:4]([NH:29][S:26]([CH3:25])(=[O:28])=[O:27])=[O:3])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 72879MethanesulfonamideHCID 738555872-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-[3-(4-fluorophenyl)-propyl]-n-methoxy-acetamide

Product 1

HCID 726130633-Hydroxy-4-methanesulfonylamino-4-oxo-but-2-enoic acid [3-(4-fluoro-phenyl)-propyl]-methoxy-amideYield 91.2%

Procedure

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.

Sources & evidence

ORD record
ord-6630402a92d0451088258a226f4977a2
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Reaction notes

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