Imidazole → HCID 22867593, compound

HRID 1902143Notes

Reaction equation

HRID 1902143 reaction equation
[OH:1][C@@H:2]([C@@H:4]1[C@@H:7]([C@H:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[S:11])[CH3:9])[NH:6][C:5]1=[O:19])[CH3:3].N1C=CN=C1.[CH2:25]([Si:27]([CH2:31][CH3:32])([CH2:29][CH3:30])Cl)[CH3:26]>CN(C)C=O.C(OCC)(=O)C>[CH2:25]([Si:27]([CH2:31][CH3:32])([CH2:29][CH3:30])[O:1][C@@H:2]([C@@H:4]1[C@@H:7]([C@H:8]([C:10]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[S:11])[CH3:9])[NH:6][C:5]1=[O:19])[CH3:3])[CH3:26]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 22867587HCID 22867587, compound

Product 1

HCID 22867593HCID 22867593, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3S,4S)-3-[(1R)-1-Hydroxyethyl]-4-[(1R)-1-p-chlorophenylthiocarbonylethyl]-2-azetidinone (477 mg, 1.51 mmol) is dissolved in dry N,N-dimethylformamide (3 ml), and thereto are added imidazole (260 mg, 3.79 mmol) and triethylchlorosilane (456 mg, 3.0 mmol), and the mixture is stirred at room temperature for five hours. The reaction solution is diluted with ethyl acetate (30 ml) and washed with water. The aqueous layer is extracted with ethyl acetate (20 ml), and the organic layers are combined, washed twice with brine, dried over sodium sulfate, and evaporated to remove the solvent. The resulting oily residue is purified by silica gel chromatography to give (3S,4S)-3-[(1R)-1-triethylsilyloxyethyl]-4-[(1R)-1-p-chlorophenylthiocarbonylethyl]-2-azetidinone (342 mg).

Workup

  1. washwashed with water
  2. extractionThe aqueous layer is extracted with ethyl acetate (20 ml)
  3. washwashed twice with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent
  7. customThe resulting oily residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-583c6724fbe247bc8d3d3aae2190bd74
Source dataset
uspto-grants-1996_11
Patent number
US05578722

Reaction notes

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