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 216410Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-8ae6be2b632e4253b38d3f951ac003b8
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193228B2

Reaction notes

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