Ammonia → (4-{[2,2-Dimethyl-4-(methylamino)butanoyl]amino}butyl) (triphenyl)phosphonium bromide

Participants

Reaction Steps

8,8,11,14,14-pentamethyl-7,12-dioxo-1,1,1-triphenyl-13-oxa-6,11-diaza-1-phosphoniapentadecane bromide (205 mg, 0.32 mmol) was dissolved in methylene chloride (1.0 mL) and methanol (0.10 mL). The solution at room temperature was treated with 2.0 M hydrogen chloride in diethyl ether (0.36 mL, 0.71 mmol). The reaction was stirred overnight at room temperature, cooled with an ice bath, and treated with 7N ammonia in methanol (0.13 mL, 0.93 mmol). After 30 minutes, the slurry that resulted was filtered, and the solids were washed with methylene chloride. The filtrate was concentrated to give the title compound (170 mg, 98%) as a white foam. The product of step 2 was used crude in next step.

Provenance & Evidence