Diethyl Ether → HCID 54406267, compound

Participants

Reaction Conditions

Reaction Steps

(S)-4-Methyl-2-[(4-phenyl-piperazine-1-carbonyl)-amino]pentanoic acid (0.300 g, 0.940 mmol) was dissolved in dry DMF (4 mL) under nitrogen atmosphere and cooled to 0° C. in an ice-water bath. To this solution were added, in succession, N,N-diisopropylethylamine (0.490 mL, 2.81 mmol) and solid O-benzotriazol-1-yl-N,N,N,′,N′-tetramethyluronium hexafluorophosphate (0.356 g, 0.939 mmol). The resulting reaction mixture was stirred at that temperature for 30 minutes; solid 4,4-bis-(4-fluoro-phenyl)-butylamine monohydrochloride (0.280 g, 0.940 mmol) was then added. After stirring for, sequentially, 10 minutes at 0° C. and 35 minutes at ambient temperature, reaction mixture was mixed with 60 mL of diethyl ether; the resulting mixture was successively washed with saturated aqueous NaHCO3 solution (2×60 mL), brine (2×60 mL), and was dried over Na2SO4. The solution was concentrated in vacuo affording a solid. Recrystallization from ether afforded 0.18 g (34%) of the pure titled compound as a white solid; mp 138-141° C. APCI-MS m/z 563.4 (MH+).

Provenance & Evidence