Sodium Hydroxide → HCID 86593313, compound

HRID 1610757Notes

Reaction equation

HRID 1610757 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12]C(=O)[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]2[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])=[CH:24][CH:23]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>CO.O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:12])[CH:9]([NH:10][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])=[CH:26][CH:27]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86593312tert-butyl (4RS,5SR)-5-(3-chlorophenyl)-2-oxo-4-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]-1,3-oxazolidine-3-carboxylate

Product 1

HCID 86593313HCID 86593313, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (4RS,5SR)-5-(3-chlorophenyl)-2-oxo-4-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]-1,3-oxazolidine-3-carboxylate (2.66 g, 5.12 mmol) in methanol-tetrahydrofuran (20 ml-20 ml) was added 1N sodium hydroxide (6.2 ml, 6.2 mmol), and the mixture was stirred overnight at room temperature. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by recrystallization (hexane-ethyl acetate) to give tert-butyl (1RS,2SR)-2-(3-chlorophenyl)-2-hydroxy-1-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]ethylcarbamate (2.11 g, 83%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by recrystallization (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-8daa6c705aeb45f18ecac82f4ff08eb5
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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