Benzyl Bromide → HCID 58237506, compound

HRID 885314Notes

Reaction equation

HRID 885314 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[CH2:23][N:24]1[C@@H:28]([CH3:29])[C@@H:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:26][C:25]1=[O:36].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:43](Br)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C=O)C>[CH2:43]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:8][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)=[C:3]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:14]=2[CH2:23][N:24]2[C@@H:28]([CH3:29])[C@@H:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:26][C:25]2=[O:36])[CH:4]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 58237643HCID 58237643, compound

Product 1

HCID 58237506HCID 58237506, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To {4-hydroxy-3-[2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid (0.07 g, 0.14 mmol) and cesium carbonate (0.09 g, 0.28 mmol) in DMF was added benzyl bromide (0.03 mL, 0.28 mmol), and the reaction was stirred at room temperature for 3 days. The mixture was partitioned between H2O and EtOAc, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the desired product.

Workup

  1. customThe mixture was partitioned between H2O and EtOAc
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ba39ca55ff774d67945eff8d08e0de9c
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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