Ammonia → N3-methyl-N-[4-(triphenylphosphonio)butyl]-beta-alaninamide bromide

Participants

Reaction Steps

N3-(tert-butoxycarbonyl)-N3-methyl-N-[4-(triphenylphosphonio)butyl]-β-alaninamide bromide (1.08 g, 1.80 mmol) was dissolved in methylene chloride (5.4 mL) and methanol (0.54 mL). The solution at room temperature was treated with 2.0 M hydrogen chloride in diethyl ether (1.98 mL, 3.96 mmol). The mixture was stirred overnight at room temperature, then cooled with an ice bath and treated with 7N ammonia in methanol (0.75 mL, 5.22 mmol). After 30 minutes, the resulting slurry was filtered, and the solids were washed with methylene chloride. The filtrate was concentrated to give the title compound (980 mg, 110%, 84% pure) as a white foam. The product of step 2 was used crude in the next step.

Provenance & Evidence