Water → HCID 22261612, compound

HRID 1610523Notes

Reaction equation

HRID 1610523 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]=[C:18]([CH3:20])[CH:17]=[C:16]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:15]=2)C(O)=O)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.C([N:48]([CH2:51]C)CC)C.[OH2:53]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:53][C:51](=[O:36])[NH:48][CH:9]2[CH2:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([O:21][C:22]([F:27])([F:26])[CH:23]([F:24])[F:25])[CH:15]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17862202HCID 17862202, compound

Product 1

HCID 22261612HCID 22261612, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-methyl-3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)propionic acid (5.8 g, 14.3 mmol) in tetrahydrofuran (100 ml) were added diphenylphosphoryl azide (3.4 ml, 15.8 mmol) and triethylamine (3.0 ml, 21.5 mmol), and the mixture was heated under reflux for 30 min. 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 (hexane:ethyl acetate=1:1) and recrystallized from ethyl acetate-hexane to give (4RS,5SR)-5-(4-fluorophenyl)-4-((5-methyl-3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-1,3-oxazolidin-2-one (4.1 g, 71%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  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 (hexane:ethyl acetate=1:1)
  9. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1dd656d9e3f14a058d9e822e493cc0fa
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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