Ammonium Acetate → HCID 54528297, compound

Participants

Reaction Steps

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.

Provenance & Evidence