Water → N-carbamimidoyl-1-[(2S)-1-hydroxy-4-phenylbutan-2-yl]imidazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of 28% NaOMe in methanol (583 mg) was added to an ice cooled solution of guanidine hydrochloride (307 mg) in DMF (5 ml). After 10 minutes, methyl (S)-1-[1-(tert-butyl-dimethylsilyloxy)-4-phenyl-2-butyl]imidazole-4-carboxylate (obtained in Example 6) (250 mg) in DMF (2 ml) was added to the mixture and the resulting mixture was stirred at 100° C. for 5 hours. After cooling, the reaction mixture was poured into water (30 ml) and the solution was washed with ethyl acetate. The aqueous layer was purified by HP-20 (40 cc) column chromatography eluting with water/2-propanol (9:1) and lyophilized to give (S)-1-[1-hydroxy-4-phenyl-2-butyl]imidazole-4-carbonylguanidine (55.4 mg)

Provenance & Evidence