Imidazole → HCID 57291415, compound

HRID 465345Notes

Reaction equation

HRID 465345 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([OH:16])[CH2:13][C:12]1=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([O:16][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:13][C:12]1=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57134164HCID 57134164, compound

Product 1

HCID 57291415HCID 57291415, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4S)-N-benzyloxycarbonyl-4-hydroxy-2-pyrrolidone (116 g), t-butyldimethylsilyl chloride (81.4 g), imidazole (67.4 g) and dimethylformamide (350 ml) is stirred at room temperature for 17 hours, and the solvent is evaporated in vacuo. To the residue is added ethyl acetate, and the mixture is washed with water, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent, n-hexane :ethyl acetate=4:1 to 2:1) to give (4S)-N-benzyloxycarbonyl-4-t-butyldimethylsilyloxy-2-pyrrolidone (160 g) as colorless needles.

Workup

  1. customthe solvent is evaporated in vacuo
  2. additionTo the residue is added ethyl acetate
  3. washthe mixture is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent, n-hexane :ethyl acetate=4:1 to 2:1)

Sources & evidence

ORD record
ord-14f57381c0f645e0806639a16dbf49fc
Source dataset
uspto-grants-1992_10
Patent number
US05153187

Reaction notes

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