Diisopropylethylamine → 3-{4-[1-Allyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid methyl ester

Participants

Reaction Steps

A solution of 4-[1-allyl-1-(4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoic acid (0.044 g, 0.094 mmol), beta-alanine, hydrochloride salt (0.0189 g, 0.135 mmol), and 1-hydroxybenzotriazole hydrate (0.0193 g, 0.143 mmol) in DMF (2.0 mL) is treated with N,N-diisopropylethylamine (0.0480 mL, 0.275 mmol), then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.0278 g, 0.145 mmol) and stirred overnight. The reaction mixture is diluted with water (5 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts are washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 10% EtOAc to 75% EtOAc to provide 0.0298 g (58%) of the title compound as a clear film. MS (ES): 552.2 [M+H]−.

Provenance & Evidence