Tetrahydrofuran → HCID 57388934, compound

Participants

Reaction Steps

A round bottom flask was charged with (R)-methyl 3-(6-(3-methyl-1-(4′-(trifluoromethyl)biphenyl-4-yl)butylamino)nicotinamido)propanoate (6.26 g, 10.2 mmol), tetrahydrofuran (60 mL) and methanol (60 mL). 1.0N NaOH (18.3 mL, 18.3 mmol) was added and the resulting solution was stirred at room temperature for 15 min. The organic solvents were removed under reduced pressure and the resulting crude was diluted with water. 10% Citric acid was added to acidify the solution to pH ˜3. A white precipitate formed. After stirring for 30 minutes at room temperature, the solid was filtered off and dried under vacuum. Purification by column chromatography (0-10% methanol/dichloromethane) provided (R)-3-(6-(3-methyl-1-(4′-(trifluoromethyl)biphenyl-4-yl)butylamino)nicotinamido)propanoic acid (25.7 g, 76.4%) as a white solid. 1H NMR (400 MHz, (CD3)2SO, δ): 0.91 (d, J=6.44 Hz, 3H) 0.95 (d, J=6.44 Hz, 3H) 1.48-1.59 (m, 1H) 1.61-1.71 (m, 1H) 1.72-1.82 (m, 1H) 2.44 (t, J=7.12 Hz, 2H) 3.34-3.42 (m, 2H) 5.10 (br. s., 1H) 6.52 (d, J=8.78 Hz, 1H) 7.46-7.51 (m, 2H) 7.57 (d, J=8.19 Hz, 1H) 7.63-7.69 (m, 2H) 7.74 (dd, J=8.88, 2.44 Hz, 1H) 7.76-7.81 (m, 2H) 7.83-7.89 (m, 2H) 8.15 (t, J=5.46 Hz, 1H) 8.40 (d, J=2.34 Hz, 1H) 12.18 (br. s., 1H). MS (M+1): 500.4.

Provenance & Evidence