Iodoethane → HCID 66892231, compound

HRID 456221Notes

Reaction equation

HRID 456221 reaction equation
[OH:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[CH2:18][N:19]2[C@@H:23]([CH3:24])[C@@H:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:21][C:20]2=[O:31])=[CH:6][C:5]([CH2:32][C:33]([OH:35])=[O:34])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:43][CH3:44].[CH3:45][C:46]#N>>[CH2:45]([O:34][C:33](=[O:35])[CH2:32][C:5]1[CH:6]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][C:9]=2[CH2:18][N:19]2[C@@H:23]([CH3:24])[C@@H:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:21][C:20]2=[O:31])[C:2]([O:1][CH2:43][CH3:44])=[CH:3][CH:4]=1)[CH3:46]

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 66890151HCID 66890151, compound

Product 1

HCID 66892231HCID 66892231, compound

Procedure

To a suspension of [6-hydroxy-2′-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid (0.085 g, 0.18 mmol) and cesium carbonate (0.171 g, 0.53 mmol) in MeCN was added iodoethane (0.03 mL, 0.35 mmol), and the reaction was stirred at room temperature. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was separated and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

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

Sources & evidence

ORD record
ord-9e735c2ceb7847eeb7d221cbd7487e70
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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