[(S)-2-(3,5-Bis-trifluoromethyl-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid benzyl ester → (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one

HRID 456218Notes

Reaction equation

HRID 456218 reaction equation
C([O:8][C:9](=O)[NH:10][C@@H:11]([CH3:28])[CH:12]([C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)[OH:13])C1C=CC=CC=1.[OH-].[K+].C1COCC1.CO>CCOC(C)=O.[Cl-].[Na+].O>[F:26][C:24]([F:25])([F:27])[C:16]1[CH:15]=[C:14]([C@H:12]2[O:13][C:9](=[O:8])[NH:10][C@H:11]2[CH3:28])[CH:19]=[C:18]([C:20]([F:22])([F:23])[F:21])[CH:17]=1

Participants

5

Reactant 2

HCID 58604019[(S)-2-(3,5-Bis-trifluoromethyl-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid benzyl esterHCID 86630533KOH MeOH THF

Product 1

HCID 23583229(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To [(S)-2-(3,5-bis-trifluoromethyl-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid benzyl ester (11.9 mmol) was added 7.5N aqueous KOH:THF:MeOH (1:4:2; 60 mL), and the reaction was stirred at room temperature for 3 hours. Once no starting material was seen by analytical LCMS, the mixture was diluted with EtOAc and brine, and the organic layer was separated and purified by silica gel chromatography to give the title compound.

Workup

  1. customthe organic layer was separated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-beff7375a8644ed6a23dc488e130ca14
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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