Pyridine → HCID 58823001, compound

Participants

Reaction Steps

Trifluoroacetic anhydride (0.043 mL, 0.37 mmol) and pyridine (0.074 mL, 0.93 mmol) were added to a solution of 3-{4-[3-(biphenyl-4-yloxy)-propoxy]-2-fluoro-phenyl}-3-hydroxy-2-methoxy-propionic acid methyl ester (0.142 g, 0.31 mmol) in methylene chloride (1 mL) at 0° C. The resulting mixture was stirred for 4 hours at room temperature and was concentrated under vacuum. The residue was dissolved in ethyl acetate (50 mL) and 10% palladium on carbon (0.064 g) was added to the solution. The mixture was stirred under hydrogen pressure (5 atm) for 16 hours. The mixture was filtered through celite and concentrated under vacuum. The residue was purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 4:1) to give 3-{4-[3-(biphenyl-4-yloxy)-propoxy]-2-fluoro-phenyl}-2-methoxy-propionic acid methyl ester as a white solid (30 mg, 22%). 1H NMR (200 MHz, CDCl3): 7.60–7.50 (m, 4H); 7.46–7.27 (m, 3H); 7.18–7.09 (m, 1H); 7.03–6.96 (m, 2H); 6.70–6.61 (m, 2H); 4.17 (dt, 4H, J=9.1, 6.2); 4.00 (dd, 1H, J=7.3, 5.9); 3.74 (s, 3H); 3.37 (s, 3H); 3.13–2.93 (m, 2H); 2.28 (qn, 2H, J=6.2).

Provenance & Evidence