Potassium Carbonate → tert-Butyl 3-[5-acetyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylate

HRID 1896641Notes

Reaction equation

HRID 1896641 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([N+:25]#[C-:26])S(C2C=CC(C)=CC=2)(=O)=O)=[CH:10][CH:9]=1.[O:27]=[C:28]([CH3:42])/[CH:29]=[N:30]/[CH:31]1[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:32]1>CN(C=O)C>[C:28]([C:29]1[N:30]([CH:31]2[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:32]2)[CH:26]=[N:25][C:14]=1[C:11]1[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=1)(=[O:27])[CH3:42]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10827289a-Tosyl-(4-fluorobenzyl) isocyanideHCID 178468239HCID 178468239, compound

Product 1

HCID 57461730tert-Butyl 3-[5-acetyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (15.0 g, 108 mmol) was added to a solution of 1-fluoro-4-{isocyano[(4-methylphenyl)sulfonyl]methyl}benzene (C2, see Organic Syntheses; Wiley & Sons: New York, 2004; Collect. Vol. 10, p. 692) (12.5 g, 43.2 mmol) and tert-butyl 3-{[(1E)-2-oxopropylidene]amino}azetidine-1-carboxylate (C1) (10 g, 44 mmol) in DMF (150 mL). The mixture was stirred for 16 hours at room temperature, then partitioned between ethyl acetate (500 mL) and water (500 mL). The organic layer was washed with water (3×500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Eluant: 1:1 petroleum ether: ethyl acetate) to give the product as a solid. Yield: 11 g, 31 mmol, 72%.

Workup

  1. custompartitioned between ethyl acetate (500 mL) and water (500 mL)
  2. washThe organic layer was washed with water (3×500 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (Eluant: 1:1 petroleum ether: ethyl acetate)

Sources & evidence

ORD record
ord-3b44c00e48ca4bac8f666585e2bac85c
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

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