Imidazole → HCID 11000905, compound

Participants

Reaction Conditions

Reaction Steps

The compound of Example 8A (0.74 g, 4.1 mmol) was dissolved in 4 mL of dimethylformamide; 0.4 g of imidazole was added, followed by 0.7 g of tert-butyldimethylsilyl chloride. The resultant mixture was stirred at ambient temperature for 4 hours; equal portions of tert-butyldimethylsilyl chloride and imidazole were added, and the mixture was heated overnight at 60° C. Water was added; the mixture was stirred at ambient temperature for 30 minutes, and then extracted with ether. The organic phase was washed sequentially with 1 N aqueous H3PO4, water, and brine, and dried over Na2SO4. The solvents were removed in vacuo, and the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with a gradient of 0% to 10% ethyl acetate in hexanes. The titled compound was isolated contaminated with some unreacted starting material (0.31 g, 42%).

Provenance & Evidence