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

HRID 1610547Notes

Reaction equation

HRID 1610547 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:34])[CH:16]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:33])([F:32])[CH:29]([F:31])[F:30])[CH:22]=2)C(O)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:54]([CH2:57]C)CC)C.[OH2:59]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[O:34][C:57](=[O:59])[NH:54][CH:16]2[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:33])([F:32])[CH:29]([F:30])[F:31])[CH:22]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22262132HCID 22262132, compound

Product 1

HCID 22262007(4RS,5SR)-5-[4-(benzyloxy)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-(benzyloxy)phenyl]-3-hydroxy-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoic acid (21.0 g, 43.9 mmol) in tetrahydrofuran (300 ml) were added diphenylphosphoryl azide (10.4 ml, 48.3 mmol) and triethylamine (9.2 ml, 65.9 mmol), ant the mixture was heated under reflux for 2 hrs. The reaction solution was allowed to cool and water (400 ml) was added. The mixture was extracted with ethyl acetate (200 ml×2). The extract was washed successively with 1N hydrochloric acid, aqueous sodium hydrogen carbonate and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1). Recrystallization from ethyl acetate-hexane gave the objective substance (16.4 g, 79%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. temperatureto cool
  4. extractionThe mixture was extracted with ethyl acetate (200 ml×2)
  5. washThe extract was washed successively with 1N hydrochloric acid, aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  9. customRecrystallization from ethyl acetate-hexane
  10. customgave the objective substance (16.4 g, 79%)

Sources & evidence

ORD record
ord-c1f6cd418d774b9baf24e51e5c708687
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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