Sulfuric Acid → 4(S)-(3,4-difluorophenyl)-5(S)-methyloxazolidin-2-one

HRID 842312Notes

Reaction equation

HRID 842312 reaction equation
[C:1](=[O:4])([O-])[O-:2].[Cs+].[Cs+].C(=O)(OO)N.S(=O)(=O)(O)O.[F:17][C:18]1[CH:19]=[C:20]([CH:25]([NH2:29])[CH:26](O)[CH3:27])[CH:21]=[CH:22][C:23]=1[F:24]>O>[F:17][C:18]1[CH:19]=[C:20]([C@H:25]2[C@H:26]([CH3:27])[O:2][C:1](=[O:4])[NH:29]2)[CH:21]=[CH:22][C:23]=1[F:24]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 10796Cesium carbonateHCID 107262321-Amino-1-(3,4-difluorophenyl)propan-2-olHCID 22345099Carbamoperoxoic acid

Product 1

HCID 105127504(S)-(3,4-difluorophenyl)-5(S)-methyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Recovery Procedure B. Cesium carbonate (2 g) was added to another portion of the hydroxy carbamate mixture, and after about thirty minutes at room temperature the reaction mixture was diluted with water (50 ml). Sulfuric acid (10 eq.) was then added, and the mixture was refluxed for 30 minutes to obtain a mixture of the title compound plus 1-(3,4-difluorophenyl)-2-hydroxy-propylamine. Isolation by neutralization with NaOH to a pH=8-9, and extraction with MTBE afforded the title compound, which was obtained in 90% ee by evaporative removal of the MTBE.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. customto obtain

Sources & evidence

ORD record
ord-08a4cb69a3684679b3c48f9e3f06dd56
Source dataset
uspto-grants-2002_04
Patent number
US06372911B1

Reaction notes

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