Water → HCID 67271574, compound

HRID 600853Notes

Reaction equation

HRID 600853 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13](=[O:25])[NH:14][C:15]2[CH:16]=[N:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:27])[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:31][CH3:32].O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13](=[O:25])[N:14]([CH2:31][CH3:32])[C:15]2[CH:16]=[N:17][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:27])[CH3:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 67271300HCID 67271300, compound

Product 1

HCID 67271574HCID 67271574, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of (R)-2,2-dimethyl-4-(6-trifluoromethyl-pyridin-3-ylcarbamoyl)-oxazolidine-3-carboxylic acid tert-butyl ester (0.20 g, 0.51 mmol) in dimethylsulfoxide (4 ml) under an argon atmosphere was added sodium hydride (0.028 g, 0.59 mmol) and the mixture was stirred for 20 min. Iodoethane (0.05 ml, 0.61 mmol) was added and the mixture was stirred overnight at room temperature. Water (20 ml) was added and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried (MgSO4) and filtered. After removal of the solvent the residue was purified by column chromatography (SiO2, heptane/EtOAc=1:1) to yield a light yellow oil (0.15 g, 70%), MS (ISP): 418.2 ([M+H]+).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customAfter removal of the solvent the residue
  6. customwas purified by column chromatography (SiO2, heptane/EtOAc=1:1)

Sources & evidence

ORD record
ord-c61167873f0c4d0ebf7d1caa39177c7a
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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