Sodium Hydroxide → HCID 22261569, compound

HRID 1610568Notes

Reaction equation

HRID 1610568 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[O:19]C(=O)[NH:17][CH:16]2[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])[CH:23]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[NH2:17][CH:16]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:33])([F:34])[CH:30]([F:31])[F:32])[CH:23]=1)[CH:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)[OH:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261541HCID 22261541, compound

Product 1

HCID 22261569HCID 22261569, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-[3-(benzyloxy)phenyl]-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one (6.5 g, 13.7 mmol) in ethanol (70 ml) was added 8N aqueous sodium hydroxide solution (5.13 ml, 41 mmol), and the mixture was heated under reflux for 4 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 (anhydrous magnesium sulfate) and evaporated under reduced pressure to give the objective substance (6.26 g, 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 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 (anhydrous magnesium sulfate)
  8. customevaporated under reduced pressure
  9. customto give the objective substance (6.26 g, 100%)

Sources & evidence

ORD record
ord-75c7ec48a5d74e28852421eb3c6377fc
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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