Trifluoroacetic acid → [(S)-2-(3,5-Bis-trifluoromethyl-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid benzyl ester

HRID 456217

Reaktionsgleichung

FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16](=[O:36])[NH:17][C@@H:18]([CH3:35])[C:19]([C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C[SiH](C)C1C=CC=CC=1.[OH-].[K+]>CCOC(C)=O.[Cl-].[Na+].O.C1COCC1>[CH2:8]([O:15][C:16](=[O:36])[NH:17][C@@H:18]([CH3:35])[CH:19]([C:21]1[CH:22]=[C:23]([C:31]([F:32])([F:33])[F:34])[CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1)[OH:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Trifluoroacetic acid (11 mL) was cooled to −5° C. [(S)-2-(3,5-Bis-trifluoromethyl-phenyl)-1-methyl-2-oxo-ethyl]-carbamic acid benzyl ester (5 g, 11.9 mmol) was added slowly, followed by dimethylphenylsilane (2.2 mL, 14.3 mmol), and the mixture was stirred for 4 hours. Once no starting material was seen by analytical tlc, the mixture was cooled to 0° C. and treated with 50% aqueous KOH (12 mL), followed by THF (16 mL). After stirring at room temperature for 5 hours, only starting material was seen by analytical tlc, and so the solution was diluted with EtOAc and brine. The organic layer was separated and concentrated, and the crude material was purified by silica gel chromatography to give the title compound.

Aufarbeitung

additionwas added slowly
stirringAfter stirring at room temperature for 5 hours
customThe organic layer was separated
concentrationconcentrated
customthe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-e2a23c883e554802a7ea3f3a7bbf9332
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08497381B2

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