Water → (4RS,5SR)-5-[4-(methylsulfonyl)phenyl]-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one

HRID 1610679Notes

Reaction equation

HRID 1610679 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:30])[CH:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])[CH:18]=2)C(O)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:50]([CH2:53]C)CC)C.[OH2:55]>O1CCCC1>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[O:30][C:53](=[O:55])[NH:50][CH:12]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:28])([F:29])[CH:25]([F:27])[F:26])[CH:18]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261576HCID 22261576, compound

Product 1

HCID 22261919(4RS,5SR)-5-[4-(methylsulfonyl)phenyl]-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoic acid (2.20 g, 4.88 mmol) in tetrahydrofuran (20 ml) were added diphenylphosphoryl azide (1.37 ml, 6.35 mmol) and triethylamine (0.95 ml, 6.84 mmol) and the mixture was stirred at room temperature for 1 hr. After heating under reflux for 1 hr, water (100 ml) was added and the mixture was extracted, with ethyl acetate (100 ml×2). The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1-1:3). Hexane was added to the precipitated crystals and the mixture was filtered to give the objective substance (2.07 g, 95%).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 1 hr
  3. extractionthe mixture was extracted, with ethyl acetate (100 ml×2)
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1-1:3)
  8. additionHexane was added to the precipitated crystals
  9. filtrationthe mixture was filtered
  10. customto give the objective substance (2.07 g, 95%)

Sources & evidence

ORD record
ord-0fcb27639a3d4a199f65996de9651930
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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