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

HRID 842312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842312
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-08a4cb69a3684679b3c48f9e3f06dd56
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372911B1

Notizen zur Reaktion

Wird geladen…