Dimethylformamide → HCID 86603603, compound

Participants

Reaction Conditions

Reaction Steps

To a stir bar equipped flask containing 4-(2,5-difluorophenyl)-6-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridne (1-5, 0.06 g, 0.19 mmol) under nitrogen was added DMF (10 mL) successively followed by N-(tert-butoxycarbonyl)-L-valine (0.08 g, 0.39 mmol), TEA (0.14 mL, 0.99 mmol), and PyBop (benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate) (0.20 g, 0.39 mmol). The resulting solution stirred at 23° C. over 72 h. Upon completion, the reaction was diluted with dichloromethane (20 mL) and washed with aqueous sodium chloride (3×50 mL). The organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash column chromatography (SiO2, 0-30% EtOAc/hexanes gradient) to give tert-butyl (1S)-3-[4-(2,5-difluorophenyl)-6-(3-methoxyphenyl)-3,6-dihydropyridin-1(2H)-yl]-1-isopropyl-2-oxopropylcarbamate (2-1). MS 445.0 found, 445.5 required (MH+−C(CH)3).

Provenance & Evidence