Imidazole → HCID 66975401, compound

HRID 1022662Notes

Reaction equation

HRID 1022662 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]([OH:15])[CH:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])([CH3:26])[CH3:25].N1C=CN=C1>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:14][CH:13]([O:15][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:30])[CH3:29])[CH:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[O:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 66976332HCID 66976332, compound

Product 1

HCID 66975401HCID 66975401, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a solution of (6RS,7SR)-4-benzyl-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-ol (27.7 g) in DMF (154 mL) were added tert-butylchlorodimethylsilane (17.8 g) and imidazole (10.7 g), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water-ethyl acetate for partitioning, and the organic layer was washed with distilled water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (37.0 g).

Workup

  1. customfor partitioning
  2. washthe organic layer was washed with distilled water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fa5f128aadd346838d5fd9ca5702763e
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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