Methanesulfonamide → 3-Hydroxy-4-methanesulfonylamino-4-oxo-but-2-enoic acid (2-isopropoxy-benzyl)-methoxy-amide
Reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]([CH3:23])[CH3:22])[O:11][CH3:12])=[O:9])[C:4](=O)[O:3]1.[CH3:26][S:27]([NH2:30])(=[O:29])=[O:28]>>[CH:21]([O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:10]([O:11][CH3:12])[C:8](=[O:9])[CH:7]=[C:5]([OH:6])[C:4]([NH:30][S:27]([CH3:26])(=[O:29])=[O:28])=[O:3])([CH3:23])[CH3:22]Participants
3
Procedure
Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(2-isopropoxy-benzyl)-N-methoxy-acetamide (0.234 g, 0.67 mmol) with methanesulfonamide (0.064 g, 0.67 mmol) as described in the preparation of compound 22 gave 0.135 g (53% yield) of the title amide as a light yellow solid. 1H NMR (400 MHz, DMSO) δ: mixture of rotamers: 1.25 and 1.30 (2×3H, 2 d, J=6 Hz, CH3), 2.86 and 2.88 (3H, 2 S, SO2CH3), 3.63 and 3.67 (3H, 2 s, OCH3), 4.62 (1H, m, CH), 4.76 (2H, s, NCH2), 6.19 and 6.23 (1H, 2 s, CH), 6.8-7.2 (4H, m, aromatics). HRMS (ESI/neg) calculated for C16H21N2O7S: [M−H]−: 385.106948; found: 385.106655.
Sources & evidence
- ORD record
- ord-675ce6c0528147989732c869cf1f3f47
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06890942B2
Reaction notes
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