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

HRID 1610270Notes

Reaction equation

HRID 1610270 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][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[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:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261726(2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(3-trifluoromethylbenzyl)propionic acid

Product 1

HCID 22262229(4RS,5SR)-5-(4-fluorophenyl)-4-((3-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-oneYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(3-trifluoromethylbenzyl)propionic acid (5.85 g, 17.1 mmol) in tetrahydrofuran (100 ml) were added diphenylphosphoryl azide (4.78 ml, 22.2 mmol) and triethylamine (3.33 ml, 23.9 mmol). The reaction solution was-heated under reflux for 4 hrs. After cooling, water (200 ml) was added, and the mixture was extracted with ethyl acetate (200 ml). The extract was washed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:ethyl acetate=10:1-5:1) to give (4RS,5SR)-5-(4-fluorophenyl)-4-((3-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (5.30 g, 91%) as crystals.

Workup

  1. temperatureThe reaction solution was-heated
  2. temperatureunder reflux for 4 hrs
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate (200 ml)
  5. washThe extract was washed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=10:1-5:1)

Sources & evidence

ORD record
ord-6012fb38460f4c689794b67649ba0e41
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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