1,2-Dichloroethane → HCID 24765482, compound

Participants

Reaction Steps

To a solution of 0.70 g (2.87 mmol) (S)-(+)-2-fluoro-alpha-methyl-4-biphenylacetic acid in 6.00 ml DMF was added 0.60 g (3.15 mmol) (1R)-1-(5-methoxypyridin-2-yl)ethanaminium chloride, 0.51 g (3.73 mmol) HOAT, 0.71 g (3.73 mmol) EDC, and 1.50 mL (8.60 mmol) DIEA. After 2.00 h at room temperature, the reaction mixture was diluted with CH2Cl2, washed three times with water, and washed with brine. The organic layer was dried over NaSO4, filtered and concentrated in vacuo. Purification by flash chromatography (1×14 cm silica gel, linear gradient 30-65% EtOAc:hexane) afforded (2S)-2-(2-fluoro-1,1′-biphenyl-4-yl)-N-[(1R)-1-(5-methoxypyridin-2-yl)ethyl]propanamide. 1H NMR (CDCl3, 400 MHz) δ 8.19 (m, 1H); 7.56-7.54 (m, 2H); 7.46-7.34 (m, 4H); 7.20-7.14 (m, 4H); 6.78 (br d, 1H, J=7.33 Hz); 5.09 (m, 1H); 3.85 (s, 1H); 3.60 (q, 1H, J=7.15 Hz, 14.29 Hz); 1.53 (d, 3H, J=7.14); 1.37 (d, 3H, J=6.77 Hz). HRMS (ES) exact mass calcd for C23H23FN2O2: 379.1817, Found: 379.1817.

Provenance & Evidence