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

HRID 885261Notes

Reaction equation

HRID 885261 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]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 532495662H-1,3-oxazol-2-id-4-oneHCID 58237612HCID 58237612, compound

Product 1

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

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.

Workup

  1. customThe mixture was partitioned between H2O and EtOAc
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-17ea2c6903f644829e135824420afc2a
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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