Dimethylformamide → 2-{3-[2-(2-Oxo-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-propionic acid

Reaktionsgleichung

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]1

Komponenten

Edukt 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 532495662H-1,3-oxazol-2-id-4-one

HCID 58237612HCID 58237612, Verbindung

Produkt 1

HCID 441877222-{3-[2-(2-Oxo-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-propionic acid

Versuchsvorschrift

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.