Sodium Hydroxide → HCID 22262322, compound

HRID 1610528Notes

Reaction equation

HRID 1610528 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[O:12]C(=O)[NH:10]2)=[CH:4][C:3]=1[O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25].[OH-].[Na+]>C(O)C>[NH2:10][CH:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:22][C:23]([F:27])([F:28])[CH:24]([F:25])[F:26])[CH:4]=1)[CH:13]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[OH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261901HCID 22261901, compound

Product 1

HCID 22262322HCID 22262322, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-4-((4-chloro-3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-5-(4-fluorophenyl)-1,3-oxazolidin-2-one (1.42 g, 3.37 mmol) in ethanol (20 ml) was added 8N aqueous sodium hydroxide solution (2.1 ml, 16.9 mmol), and the mixture was heated under reflux for 3 hrs. The reaction solution was concentrated, diluted with water (100 ml) and extracted with ethyl acetate (100 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give (1RS,2SR)-2-amino-3-(4-chloro-3-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-1-propanol (1.17 g, 88%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. concentrationThe reaction solution was concentrated
  4. additiondiluted with water (100 ml)
  5. extractionextracted with ethyl acetate (100 ml×2)
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6337de89dfbc4adcbb4c1fad9994d7e0
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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