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

HRID 1610646Notes

Reaction equation

HRID 1610646 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:24])[CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH:21]([CH3:23])[CH3:22])[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>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:24][C:47](=[O:32])[NH:44][CH:9]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH:21]([CH3:22])[CH3:23])[CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261453HCID 22261453, compound

Product 1

HCID 22261652(4RS,5SR)-5-(4-fluorophenyl)-4-[3-(isopropyloxy)benzyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-[3-(isopropyloxy)benzyl]propanoic acid (7.14 g, 21.5 mmol) in tetrahydrofuran (100 ml) were added diphenylphosphoryl azide (6.0 ml, 27.9 mmol) and triethylamine (4.19 ml, 30.1 mmol), and the mixture was stirred at room temperature for 1 hr. The mixture was heated under reflux for 5 hrs. and concentrated under reduced pressure. The saturated aqueous sodium hydrogen carbonate (100 ml) was added and the mixture was extracted with ethyl acetate (200 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1-2:1) to give the-objective substance (14.7 g, 91%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. concentrationand concentrated under reduced pressure
  4. additionThe saturated aqueous sodium hydrogen carbonate (100 ml) was added
  5. extractionthe mixture was extracted with ethyl acetate (200 ml)
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1-2:1)
  10. customto give the-objective substance (14.7 g, 91%)

Sources & evidence

ORD record
ord-7628e05d89bd498db3085db7268c0fa9
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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