Triethylamine → (4RS,5SR)-4-[3-(1,1-difluoroethyl)benzyl]-5-(4-fluorophenyl)-1,3-oxazolidin-2-one

HRID 1610725Notes

Reaction equation

HRID 1610725 reaction equation
[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[CH2:8][CH:9]([CH:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[OH:14])C(O)=O)([F:4])[CH3:3].C([N:27]([CH2:30]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1>O1CCCC1>[F:4][C:2]([C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[CH2:8][CH:9]1[CH:13]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[O:14][C:30](=[O:39])[NH:27]1)([F:1])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261533(2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid

Product 1

HCID 22261676(4RS,5SR)-4-[3-(1,1-difluoroethyl)benzyl]-5-(4-fluorophenyl)-1,3-oxazolidin-2-oneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid (4.22 g, 13.6 mmol) in tetrahydrofuran (130 ml) were added triethylamine (2.85 ml, 20.4 mmol) and diphenylphosphoryl azide (3.23 ml, 14.96 mmol), and the mixture was heated under reflux for 5 hrs. The solvent was evaporated, and the residue was diluted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give [4RS,5SR]-4-(3-[1,1-difluoroethyl)benzyl]-5-(4-fluorophenyl)-1,3-oxazolidin-2-one (3.99 g, 95%) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. customThe solvent was evaporated
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-5b198d0e8b554405ade0dfcbc4c245e1
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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