Water → HCID 22262075, compound

HRID 1610449Notes

Reaction equation

HRID 1610449 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([OH:24])[CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)C(O)=O)[CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:44]([CH2:47]C)CC)C.[OH2:49]>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]2[O:24][C:47](=[O:49])[NH:44][CH:9]2[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261871HCID 22261871, compound

Product 1

HCID 22262075HCID 22262075, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(6-chloro-2-pyridyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (3.1 g, 8.6 mmol) in tetrahydrofuran (100 ml) were added diphenylphosphoryl azide (2.0 ml, 9.5 mmol) and triethylamine (1.8 ml, 12.9 mmol), and the mixture was heated under reflux for 1 hr. The reaction solution was allowed to cool, water (150 ml) was added, and the mixture was extracted with ethyl acetate (150 ml×2). The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether-hexane to give 5-(6-chloro-2-pyridyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (1.18 g, 38%, (4RS,5RS) form: (4RS,5SR) form=3:2).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureto cool
  4. extractionthe mixture was extracted with ethyl acetate (150 ml×2)
  5. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was recrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-4182e43e920b464b8d1e40c9045b6db7
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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