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

HRID 1610756Notes

Reaction equation

HRID 1610756 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:28])[CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])=[CH:16][CH:15]=2)C(O)=O)[CH:5]=[CH:6][CH:7]=1.C([N:31]([CH2:34]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:28][C:34](=[O:43])[NH:31][CH:9]2[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][C:21]([F:26])([F:27])[C:22]([F:25])([F:24])[F:23])=[CH:18][CH:19]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22262096(2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionic acid

Product 1

HCID 22261848(4RS,5SR)-5-(3-chlorophenyl)-4-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]-1,3-oxazolidin-2-oneYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionic acid (2.75 g, 6.50 mmol) in tetrahydrofuran (70 ml) were added triethylamine (1.36 ml, 9.75 mmol) and diphenylphosphoryl azide (1.54 ml, 7.15 mmol), and the mixture was heated under reflux for 4 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 as recrystallized from hexane-ethyl acetate to give (4RS,5SR)-5-(3-chlorophenyl)-4-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]-1,3-oxazolidin-2-one (2.54 g, 93%) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-e99d7f5fa7cb423fb6cff27aac897866
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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