N4-Acetylsulfanilamide → 4-(4-Acetylamino-benzenesulfonylamino)-3-hydroxy-4-oxo-but-2-enoic acid (4-fluoro-benzyl)-methoxy-amide

HRID 2181102

Reaction equation

HRID 2181102 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:11][CH3:12])=[O:9])[C:4](=[O:21])O1.[S:23]([C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:36])[CH3:35])=[CH:29][CH:28]=1)(=[O:26])(=[O:25])[NH2:24]>>[F:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:10]([O:11][CH3:12])[C:8](=[O:9])[CH:7]=[C:5]([OH:6])[C:4]([NH:24][S:23]([C:27]2[CH:28]=[CH:29][C:30]([NH:33][C:34](=[O:36])[CH3:35])=[CH:31][CH:32]=2)(=[O:25])=[O:26])=[O:21])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 8482N4-AcetylsulfanilamideHCID 730332332-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide

Product 1

HCID 761691594-(4-Acetylamino-benzenesulfonylamino)-3-hydroxy-4-oxo-but-2-enoic acid (4-fluoro-benzyl)-methoxy-amide

Procedure

2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide was treated with N-(4-sulfamoyl-phenyl)-acetamide as described in the preparation of compound 1 to yield the title compound. 1H NMR (500 MHz, DMSO) δ: 2.07 (s, 3), 3.60 (s, 3), 4.71 (s, 2), 6.26 (s, 1), 6.94 (m, 2), 7.21 (m, 2), 7.72 (m, 2), 7.86 (m, 2).

Sources & evidence

ORD record
ord-9d99fefc4ecb4149843473aee44ee085
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Linked notes

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