Methanesulfonamide → 4-{[(3-Hydroxy-4-methanesulfonylamino-4-oxo-but-2-enoyl)-methoxy-amino]-methyl}-benzoic acid
Reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[O:11][CH3:12])=[O:9])[C:4](=O)[O:3]1.[CH3:25][S:26]([NH2:29])(=[O:28])=[O:27]>>[OH:6][C:5]([C:4]([NH:29][S:26]([CH3:25])(=[O:28])=[O:27])=[O:3])=[CH:7][C:8]([N:10]([CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)[O:11][CH3:12])=[O:9]Participants
3
Procedure
Reaction of 4-({[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl]-methoxy-amino}-methyl)-benzoic acid (0.125 g, 0.37 mmol) with methanesulfonamide (0.053 g, 0.55 mmol) as described for compound 1 gave 0.131 g (95%) of the title amide as a white solid after recrystallization from acetonitrile; mp 119-124° C. 1H NMR (400 MHz, DMSO) δ: (ppm)); mixture of rotamers: 2.99 and 3.09 (3H, 2 S, SO2CH3), 3.42 and 3.54 (3H, 2 s, OCH3), 4.63 and 4.76 (2H, 2 s, NCH2), 6.14 (1H, s, CH), 7.17 (2H, m, aromatics), 7.69 (2H, m, aromatics). HRMS (ESI/pos) calculated for C14H17N2O8S, [M+H]+: 373.070563; found: 373.070061. Anal. calcd for C14H16N2O8S: C, 45.16; H, 4.33; N, 7.52; found: C, 45.22; H, 4.70; N, 8.12.
Sources & evidence
- ORD record
- ord-2a72a62fedc342f08e1d39a9f7795dc2
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06890942B2
Reaction notes
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