Diisopropylethylamine → HCID 54422026, compound

Participants

Reaction Conditions

Reaction Steps

(S)-2-[(Azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid (0.56 g, 2.2 mmol) was dissolved in dry DMF (7 mL) under nitrogen atmosphere and cooled to 0° C. in an ice-water bath. To this solution were added, in succession, N,N-diisopropylethylamine (0.76 mL, 4.4 mmol) and solid O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.82 g, 2.2 mmol). The resulting reaction mixture was stirred at that temperature for 30 minutes; solid 1-bis(4-fluorophenyl)methyl piperazine (0.63 g, 2.2 mmol, Acros Organics, Pittsburgh, Pa.) was then added. After sequentially 30 minutes stirring at 0° C. and 2 hours 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 viscous oil. The crude product was further purified by flash chromatography (60% EtOAc in hexane) to provide 1.1 g (96%) of the pure titled compound as a white foam: mp 78-86° C. APCI-MS m/z 527.0 (MH+).

Provenance & Evidence