Diisopropylethylamine → (2S,4R)-methyl 1-((S)-2-((but-3-enyloxy)carbonylamino)-3,3-dimethylbutanoyl)-4-methoxy-4-(2-vinylbiphenyl-4-yl)pyrrolidine-2-carboxylate

Participants

Reaction Steps

(S)-2-((but-3-enyloxy)carbonylamino)-3,3-dimethylbutanoic acid (117 mg, 0.511 mmol), DIEA (0.179 mL, 1.022 mmol) and HATU (143 mg, 0.375 mmol) were added to a solution of (2S,4R)-methyl 4-methoxy-4-(2-vinylbiphenyl-4-yl)pyrrolidine-2-carboxylate (115 mg, 0.341 mmol) in DCM (4 mL). The reaction was stirred at r.t. overnight. The reaction was evaporated and purified by flash chromatography on the Biotage (0-40% EtOAc:Hex) to give (2S,4R)-methyl 1-((S)-2-((but-3-enyloxy)carbonylamino)-3,3-dimethylbutanoyl)-4-methoxy-4-(2-vinylbiphenyl-4-yl)pyrrolidine-2-carboxylate (150 mg, 0.273 mmol, 80% yield) as a white foam. LCMS: rt=1.89 min. [M+Na]+=571; Phenomenex-Luna C-18 (5μ) (3.0×50 mm); Solvent A=10% acetonitrile—90% water—0.1% TFA, Solvent B=90% acetonitrile—10% water—0.1% TFA; gradient 0% to 100% solvent B over 2 min. and then hold for 1 min.; 4 mL/min; inj. vol.=5 uL; wavelength=220.

Provenance & Evidence