Sodium Methoxide → HCID 178508316, compound

Participants

Reaction Steps

A solution of 28% NaOMe in methanol (772 mg) was added to an ice cooled solution of aminoguanidine hydrochloride (332 mg) in methanol (5 ml). After 10 minutes, methyl (S)-1-[1-(tert-butyldimethylsilyloxy)-4-phenyl-2-butyl]-imidazole-4-carboxylate (obtained in Example 6) (389 mg) in methanol (2 ml) was added to the mixture and the resulting mixture was stirred at reflux for 22 hours. After cooling, the insoluble material was removed and then the filtrate was evaporated. The residue was diluted with water and the solution was acidified to pH 4 with 6N HClaq. The resulting mixture was washed with CHCl3. The aqueous layer was purified by HP-20 (50 cc) column chromatography eluting with water/2-propanol (9:1) and lyophilized to give (S)-2-[4-(5-amino-1,2,4-triazol-3-yl)-1-imidazolyl]-4-phenylbutan-1-ol (107 mg).

Provenance & Evidence