Water → HCID 10310667, compound

Participants

Reaction Steps

1M solution of tetrabutylammonium fluoride in THF (0.387 ml) was added to a solution of 1-{(3R,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-4-benzoxazolyl]-3-pentyl}imidazole-4-carboxamide (E0001; 0.16 g) in THF (7 ml) and the mixture was stirred at r.t. for 2 hours. EtOAc and water were added and the organic layer was separated, washed with water, dried and evaporated. The residue (0.16 g) was chromatographed over silica gel (5 g) eluting with a mixture of dichloromethane and methanol (20:1 to 10:1). The desired product was treated with HCl in EtOAc to give a white powder of 1-{(3R,4S)-4-hydroxy-1-[2-(4-chlorophenyl)-4-benzoxazolyl]-3-pentyl}imidazole-4-carboxamide hydrochloride (E0017; 79.4 mg).

Provenance & Evidence