[(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 456218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456218
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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-beff7375a8644ed6a23dc488e130ca14
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497381B2

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