Imidazole → HCID 22864980, compound

HRID 1078732Notes

Reaction equation

HRID 1078732 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[CH:10]=[O:11].[C:13]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])([CH3:15])[CH3:14].N1C=CN=C1>CN(C)C=O.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C@@H:4]1[CH2:8][C@@H:7]([O:9][Si:17]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:19])[CH3:18])[CH2:6][N:5]1[CH:10]=[O:11]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 45116049HCID 45116049, compound

Product 1

HCID 22864980HCID 22864980, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-formyl-4-hydroxyproline methyl ester (3.46 g, 20.0 mmol) in N,N-dimethylformamide (10 ml) and methylene chloride (20 ml) were successively added tert-butylchlorodimethylsilane (3.20 g, 21.2 mmol) and imidazole (1.47 g, 21.6 mmol) under a nitrogen atmosphere under cooling with ice under stirring. The mixture was stirred at room temperature for 4 h. Then, the reaction solution was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was subjected to silica gel column chromatography (Wakogel™ C-300, heptane-ethyl acetate=1:1) to give the title compound (5.54 g, yield: 96.3%).

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture was stirred at room temperature for 4 h
  3. washThen, the reaction solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bf9ff954d2847deb55aeba97e1a5ad2
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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