Imidazole → HCID 18794886, compound

HRID 1004336Notes

Reaction equation

HRID 1004336 reaction equation
[OH:1][CH2:2][CH:3]([CH2:7][C:8]1[O:9][C:10]([C:13](=[O:21])[NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:12]=1)[CH:4]([OH:6])[CH3:5].N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[Si:27]([O:1][CH2:2][CH:3]([CH2:7][C:8]1[O:9][C:10]([C:13](=[O:21])[NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:12]=1)[CH:4]([OH:6])[CH3:5])([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 18794915HCID 18794915, compound

Product 1

HCID 18794886HCID 18794886, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

645 mg of (2RS,3SR)-3-(hydroxymethyl)-4-{5-(phenylcarbamoyl)-2-furyl}butan-2-ol in 12 ml of dimethylformamide was mixed with 305 mg of imidazole and 372 mg of tert-butyldimethylsilyl chloride under cooling with ice and stirred at the same temperature for 1 hour. Saturated aqueous ammonium chloride and ethyl acetate were added to the reaction solution for extraction, and the organic layer was washed with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1] to give 805 mg of the title compound as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. washthe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1]

Sources & evidence

ORD record
ord-0a3c75d3b14a4a86acda6d60b3d20211
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

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