C(N(CC)CC)C.[CH3:8][N:9]([CH3:14])[S:10](Cl)(=[O:12])=[O:11].[CH3:15][C:16]([CH3:27])([CH2:25][CH3:26])[CH2:17][C:18]1[N:19]=[C:20]([CH3:24])[N:21]([OH:23])[CH:22]=1>C(Cl)Cl>[CH3:15][C:16]([CH3:27])([CH2:25][CH3:26])[CH2:17][C:18]1[N:19]=[C:20]([CH3:24])[N:21]([O:23][S:10]([N:9]([CH3:14])[CH3:8])(=[O:12])=[O:11])[CH:22]=1Triethylamine (100 mL, 0.72 mol) followed by N,N-dimethylsulfamoyl chloride (42 mL, 0.38 mol) were added to a 0° C. solution of 4-(2,2-dimethylbutyl)-2-methyl-1H-imidazol-1-ol in methylene chloride (100 mL). After stirring at ambient temperature for 2 h, the reaction mixture was washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography over silica eluting with ethyl acetate/hexane followed by methanol afforded N-({[4-(2,2-dimethylbutyl)-2-methyl-1H-imidazol-1-yl]oxy}sulfonyl)-N-methylmethanamine (ca. 50% purity by HPLC) which was dissolved in 7:1 methanol/acetic acid (400 mL), and 10% Palladium (10% on activated carbon) (6 g) was added. After stirring under 40 psi hydrogen for 2 h, the reaction mixture was filtered through celite, rinsing with methanol and concentrated in vacuo. The residue was redissolved in ethyl acetate and washed with 1 N aqueous sodium hydroxide and brine, dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 5-20% methanol/methylene chloride afforded 4-(2,2-dimethylbutyl)-2-methyl-1H-imidazole.
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