Imidazole → 5-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)pentanoic acid amide

HRID 406372Notes

Reaction equation

HRID 406372 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[CH2:5][C:6]([NH2:8])=[O:7].N1C=CN=C1.[Si:24](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O>[Si:24]([O:1][CH2:2][CH2:3][CH:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=1)[CH2:5][C:6]([NH2:8])=[O:7])([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 666188875-Hydroxy-3-(4-trifluoromethylphenyl)pentanoic acid amide

Product 1

HCID 666301385-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)pentanoic acid amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Hydroxy-3-(4-trifluoromethylphenyl)pentanoic acid amide (350 mg) was dissolved in dimethylformamide (13 mL), and imidazole (365 mg) and tert-butyldiphenylsilyl chloride (697 μL) were added at room temperature. After stirring for one hour, the reaction solution was partitioned with ethyl acetate and water. The organic layer was washed with water (twice), 1 N hydrochloric acid and brine. After drying over magnesium sulfate, concentration under reduced pressure and purification by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 90%) gave the title compound (680 mg).

Workup

  1. customthe reaction solution was partitioned with ethyl acetate and water
  2. washThe organic layer was washed with water (twice), 1 N hydrochloric acid and brine
  3. dry with materialAfter drying over magnesium sulfate, concentration under reduced pressure and purification by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 90%)

Sources & evidence

ORD record
ord-23fe19abd8914c8b86bcfed33a2e9fa4
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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