Ammonium Acetate → HCID 54528297, compound

HRID 278491Notes

Reaction equation

HRID 278491 reaction equation
[Si]([O:8][CH2:9][CH:10]([N:20]1[CH:24]=[C:23]([C:25]([NH2:27])=[O:26])[N:22]=[CH:21]1)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C([O-])(C)=O.[NH4+]>C1COCC1>[OH:8][CH2:9][CH:10]([N:20]1[CH:24]=[C:23]([C:25]([NH2:27])=[O:26])[N:22]=[CH:21]1)[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 2724141Tetrabutylammonium FluorideHCID 53697664HCID 53697664, compound

Product 1

HCID 54528297HCID 54528297, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cooled solution of 1-[1-(tert-butyldimethylsilyloxy)-4-(4-methylphenyl)-2-butyl]imidazole-4-carboxamide (obtained in Example 3(4))(194 mg, 0.50 mmol) in THF (5 ml) was added dropwise 1.0 M Bu4NF in THF (1.0 ml). After the addition was completed, the reaction mixture was stirred at ice-bath temperature for 1 h. 25% AcONH4 (4 ml) was added, and the resulting mixture was stirred for several minutes and then extracted with chloroform. The organic layer was washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel (5 g) column chromatography eluting with chloroform/methanol (20:1) to give 1-[1-hydroxy-4-(4-methylphenyl)-2-butyl]imidazole-4-carboxamide (44.9 mg, 32.9%) as a white solid.

Workup

  1. additionAfter the addition
  2. stirringthe resulting mixture was stirred for several minutes
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel (5 g) column chromatography
  8. washeluting with chloroform/methanol (20:1)

Sources & evidence

ORD record
ord-ccd4b8f3bab240ac816ae3390b34cb27
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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