Dimethylformamide → 2-{3-[2-(2-Oxo-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-propionic acid
Reaction equation
Br[CH2:2][C:3]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1.[O:25]1[CH2:29][C:28](=O)[N:27]=[C-:26]1.[H-].[Na+].CN(C=[O:37])C>>[O:37]=[C:26]1[N:27]([CH2:2][C:3]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=2[O:5][C:6]2[CH:7]=[C:8]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=2)[CH2:28][CH2:29][O:25]1Participants
5
Procedure
To 2-[3-(2-bromomethyl-4-trifluoromethyl-phenoxy)-phenyl]-propionic acid (0.042 g, 0.10 mmol) and 2-oxazolidone (0.018 g, 0.21 mmol) in DMF was added sodium hydride (60% in mineral oil; 0.008 g, 0.21 mmol), and the reaction was stirred at room temperature for 30 minutes. The mixture was partitioned between H2O and EtOAc, and the aqueous layer was acidified and purified by preparative HPLC to give the desired product.