Diisopropylethylamine → HCID 76495078, compound

Participants

Reaction Conditions

Reaction Steps

(S)-4-Methyl-2-morpholin-4-yl-pentanoic acid (0.161 g, 0.800 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-diisopropyl-ethylamine (0.420 mL, 2.41 mmol) and solid O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate (0.303 g, 0.799 mmol). The resulting reaction mixture was stirred at that temperature for 30 minutes, solid (S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide monohydrochloride (0.290 g, 0.800 mmol) was then added. After stirring for, sequentially, 10 minutes at 0° C. and 45 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 viscous oil. The crude product was further purified by flash chromatography (60% EtOAc in hexane) and treated with ethereal HCl. Subsequent concentration in vacuo, trituration with ether and drying under vacuum provided 0.27 g (62%) of the pure titled compound as a white solid.

Provenance & Evidence