Water → tert-Butyl (4R)-4-((S)-((tert-butyl(dimethyl)silyl)oxy)(4-(trifluoromethyl)phenyl)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

HRID 2075416

Reaktionsgleichung

Reaktionsgleichung von HRID 2075416
[Si:1]([O:8][C@@H:9]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)[C@H:10]1[CH2:14][O:13][S:12](=[O:15])[N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:34].[Na+].O.CCOC(C)=O>CC#N.O.[Ru](Cl)(Cl)Cl>[Si:1]([O:8][C@@H:9]([C:23]1[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=1)[C@H:10]1[CH2:14][O:13][S:12](=[O:34])(=[O:15])[N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 67089512tert-Butyl (4R)-4-((S)-((tert-butyl(dimethyl)silyl)oxy)(4-(trifluoromethyl)phenyl)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxide

Produkt 1

HCID 58488199tert-Butyl (4R)-4-((S)-((tert-butyl(dimethyl)silyl)oxy)(4-(trifluoromethyl)phenyl)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6093376Ruthenium trichloride hydrateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl (4R)-4-((S)-((tert-butyl(dimethyl)silyl)oxy)(4-(trifluoromethyl)phenyl)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxide (1.80 g, 3.63 mmol), sodium periodate (3.11 g, 14.5 mmol), ruthenium(III) chloride hydrate (0.0164 g, 0.0726 mmol) in CH3CN:water:EtOAc (51 mL:17 mL:9 mL) was put in a sonicator for 17 minutes. The dark mixture became a yellow suspension. HPLC-MS showed no more starting material. The reaction mixture was filtered through celite and the solid was washed with EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, and then concentrated in vacuo. The residue was purified by chromatography on silica gel (0-4%-10% EtOAc-hexane) to provide the product as a white solid (1.75 g, 94%). LCMS (API-ES) m/z: 456 (M+H+-56).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe solid was washed with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0-4%-10% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-75e5495fc0c044a5ac5860b45a96e167
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919504B2

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