Water → (4RS,5RS)-5-(4-fluorophenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one

HRID 1610185Notes

Reaction equation

HRID 1610185 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)C(O)=O)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C.[OH2:49]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:49][C:47](=[O:32])[NH:44][CH:9]2[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261666(2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid

Product 1

HCID 22262143(4RS,5RS)-5-(4-fluorophenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-oneYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (4.30 g, 12.6 mmol) in tetrahydrofuran (80 ml) were added diphenylphosphoryl azide (3.0 ml, 13.8 mmol) and triethylamine (2.63 ml, 18.8 mmol) and the mixture was heated under reflux for 4 hrs. The reaction solution was diluted with water (300 ml) and extracted with ethyl acetate (200 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1) and recrystallized from ethyl acetate-hexane to give (4RS,5SR)-5-(4-fluorophenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (3.55 g, 83%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. extractionextracted with ethyl acetate (200 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1)
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d32fd20b72e044ad8bd83cb3fcb4914a
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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