Imidazole → HCID 67176416, compound

HRID 2355280Notes

Reaction equation

HRID 2355280 reaction equation
N1C=CN=C1.[C:6]([O:10][C:11](=[O:22])[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]O)[CH:15]=1)([CH3:9])([CH3:8])[CH3:7].[I:23]I.C(OCC)(=O)C.ClCCl>ClCCl>[C:6]([O:10][C:11](=[O:22])[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][I:23])[CH:15]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 2794814tert-Butyl 3-(hydroxymethyl)benzylcarbamateHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 67176416HCID 67176416, compoundYield 119.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Stir polystyrene-bound triphenylphosphine (4.27 g, 12.8 mmol) and imidazole (0.86 g, 12.7 mmol) in dichloromethane (45 mL). Add a solution of (3-hydroxymethyl-benzyl)-carbamic acid tert-butyl ester (1.70 g, 6.1 mmol) in dichloromethane (45 mL). Add iodine (3.22 g, 12.7 mmol) in 3 portions. Stir 16 hrs. Filter through a pad of diatomaceous earth. Wash with aqueous sodium thiosulfate. Dry the organic portion over sodium sulfate. Filter and concentrate. Chromatograph the residue on silica eluting with 25% ethyl acetate/dichloromethane to provide the title compound (2.53 g, 7.3 mmol).

Workup

  1. filtrationFilter through a pad of diatomaceous earth
  2. washWash with aqueous sodium thiosulfate
  3. dry with materialDry the organic portion over sodium sulfate
  4. filtrationFilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-9a501b03f5b74998810076ac394213f0
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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