Water → HCID 22259335, compound

HRID 1610948Notes

Reaction equation

HRID 1610948 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[C:13]([O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[C:29]2[CH2:33][CH2:34][OH:35])=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14].O>C(OCC)(=O)C>[CH3:8][S:9]([O:35][CH2:34][CH2:33][C:29]1[N:28]([CH2:27][CH2:26][CH2:25][CH2:24][C:21]2[CH:20]=[CH:19][C:18]([O:17][C:13]([CH3:15])([CH3:14])[CH3:16])=[CH:23][CH:22]=2)[CH:32]=[CH:31][N:30]=1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22259332HCID 22259332, compound

Product 1

HCID 22259335HCID 22259335, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (3.16 ml) and methanesulfonyl chloride (1.40 ml) were added to a solution of 2-[1-[4-(4-tert-butoxyphenyl)butyl]-1H-imidazol-2-yl]ethanol (4.77 g) in ethyl acetate (50 ml) at 0° C., and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give crude 2-[1-[4-(4-tert-butoxyphenyl)butyl]-1H-imidazol-2-yl]ethyl methanesulfonate. Sodium thiomethoxide (2.25 g) was added to a solution of the product in DMF (35 ml), and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was successively washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 to 1:3) to give the titled compound (4.22 g) as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-37a417c7ca934ec3b8d6809bc6597204
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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