Sodium Sulfite → HCID 86649645, Verbindung

HRID 1257542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257542
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:27])[C:12]2[CH:17]=[C:16]([CH:18]=C)[CH:15]=[C:14]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)[CH:13]=2)[CH3:9])=[N:6][CH:7]=1.I([O-])(=O)(=O)=[O:29].[Na+].S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:27])[C:12]2[CH:13]=[C:14]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)[CH:15]=[C:16]([CH:18]=[O:29])[CH:17]=2)[CH3:9])=[N:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 66895503N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-(5-methyl-2-pyridinyl)-5-vinylbenzamide

Produkt 1

HCID 86649645HCID 86649645, VerbindungAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-(5-methyl-2-pyridinyl)-5-vinylbenzamide (1.14 g, 3.15 mmol) in tetrahydrofuran (11 mL) and water (11 mL) were added sodium periodate (2.0 g, 9.45 mmol) and osmium tetroxide (2.5% in tert-butanol, 2.0 mL, 0.157 mmol). The reaction mixture was stirred at ambient temperature for 18 h. Saturated aqueous sodium sulfite and saturated aqueous sodium bicarbonate were added. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound (1.1 g). MS 364.1 (M+1).

Aufarbeitung

  1. extractionThe mixture was extracted with dichloromethane (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5ec7cdf96ff143afb90ff6eefecb10c8
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461185B2

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