Water → HCID 22262062, compound

HRID 1610440Notes

Reaction equation

HRID 1610440 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([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: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]=[CH:6][C:5]([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:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17862261HCID 17862261, compound

Product 1

HCID 22262062HCID 22262062, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(6-chloro-3-pyridyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (5.0 g, 13.9 mmol) in tetrahydrofuran (150 ml) were added diphenylphosphoryl azide (3.3 ml, 15.3 mmol) and triethylamine (2.9 ml, 20.9 mmol), and the mixture was heated under reflux for 1 hr. The reaction solution was allowed to cool and water (200 ml) was added. The mixture was extracted with ethyl acetate (200 ml×2). The extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate-hexane to give (4RS,5SR)-5-(6-chloro-3-pyridyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (4.29 g, 87%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureto cool
  4. extractionThe mixture was extracted with ethyl acetate (200 ml×2)
  5. washThe extract was washed successively with 1N hydrochloric acid, 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 purified by silica gel column chromatography (ethyl acetate)
  9. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-30c07f85fb15443ca19138768c0cfdcd
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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