Water → (1RS,2SR)-2-amino-1-[4-(methylsulfonyl)phenyl]-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-1-propanol

HRID 1610680Notes

Reaction equation

HRID 1610680 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[O:15]C(=O)[NH:13][CH:12]2[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])[CH:19]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+].O>C(O)C>[NH2:13][CH:12]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])[CH:19]=1)[CH:11]([C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1)[OH:15]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22261919(4RS,5SR)-5-[4-(methylsulfonyl)phenyl]-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one

Product 1

HCID 22261449(1RS,2SR)-2-amino-1-[4-(methylsulfonyl)phenyl]-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-1-propanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-[4-(methylsulfonyl)phenyl]-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one (1.80 g, 4.02 mmol) in ethanol (20 ml) was added 8N aqueous sodium hydroxide solution (1.51 ml, 12.07 mmol) and the mixture was heated under reflux for 3 hrs. To the reaction solution was added water (100 ml) and the mixture was extracted with ethyl acetate (200 ml×2). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was crystallized from hexane-diethyl ether to give the objective substance (1.49 g, 86%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. extractionthe mixture was extracted with ethyl acetate (200 ml×2)
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was crystallized from hexane-diethyl ether
  8. customto give the objective substance (1.49 g, 86%)

Sources & evidence

ORD record
ord-eb9f0f7f15054830811b96e7503844e2
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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