Methanesulfonamide → 3-Hydroxy-4-methanesulfonylamino-4-oxo-but-2-enoic acid (4-fluoro-benzyl)-methoxy-amide

HRID 2181093

Reaktionsgleichung

Reaktionsgleichung von HRID 2181093
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)[O:3]1.[CH3:23][S:24]([NH2:27])(=[O:26])=[O:25]>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]([O:11][CH3:12])[C:8](=[O:9])[CH:7]=[C:5]([OH:6])[C:4]([NH:27][S:24]([CH3:23])(=[O:26])=[O:25])=[O:3])=[CH:15][CH:16]=1

Komponenten

3

Edukt 2

HCID 72879MethanesulfonamideHCID 730332332-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide

Produkt 1

HCID 726130563-Hydroxy-4-methanesulfonylamino-4-oxo-but-2-enoic acid (4-fluoro-benzyl)-methoxy-amideAusbeute 29 %

Versuchsvorschrift

2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide was treated with methane sulfonamide as described in the preparation of compound 1 to yield 100 mg solid (29% yield), mp=137° C. (decomposition). HRMS (M−H) cacld for C13H14FN2O6S: 345.056. Found: 345.0570. Anal calcd for C13H15FN2O6S: C, 45.08; H, 4.36; N, 8.08. Found: C, 45.20; H, 4.29; N, 7.92. 1H NMR (500 MHz, CDCl3) δ: 3.36 (s, 3), 3.71 (s, 3), 4.81 (s, 2), 6.56 (s, 1), 7.04 (m, 2), 7.32 (m, 2), 8.97 (s, 1). 13C NMR (125 MHz, CDCl3) δ: 41.60, 48.27, 63.16, 92.57, 115.65, 115.81, 130.19, 130.24, 130.97, 158.99, 160.05, 161.65, 163.61, 170.79.

Quellen und Nachweise

ORD-Eintrag
ord-538fa56047574cea89365fdc1f8c4726
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06890942B2

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