4-(2,2-dimethylbutyl)-2-[1-hydroxy-2-oxo-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide → 2-[1,2-dihydroxy-2-(4-pyridin-2-ylphenyl)propyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 216410

Reaktionsgleichung

[CH3:1][Mg]Br.[CH3:4][C:5]([CH3:36])([CH2:34][CH3:35])[CH2:6][C:7]1[N:8]=[C:9]([CH:18]([OH:33])[C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:22][CH:21]=2)[N:10]([S:12]([N:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:11]=1>O1CCCC1>[OH:33][CH:18]([C:9]1[N:10]([S:12]([N:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:11]=[C:7]([CH2:6][C:5]([CH3:36])([CH3:4])[CH2:34][CH3:35])[N:8]=1)[C:19]([OH:32])([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:22][CH:21]=1)[CH3:1]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Methylmagnesium bromide (3 M in diethyl ether) (28 μL, 0.09 mmol) was added to a 0° C. solution of 4-(2,2-dimethylbutyl)-2-[1-hydroxy-2-oxo-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide (20 mg, 0.04 mmol) in tetrahydrofuran (2 mL). After stirring at 0° C. until no further reaction (LCMS), the reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded 2-[1,2-dihydroxy-2-(4-pyridin-2-ylphenyl)propyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Aufarbeitung

customthe reaction mixture was quenched with saturated aqueous ammonium chloride
extractionextracted with methylene chloride
dry with materialThe combined organic extracts were dried (magnesium sulfate)
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-8ae6be2b632e4253b38d3f951ac003b8
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08193228B2

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