Potassium Sodium Tartrate → HCID 86622467, Verbindung

HRID 606800

Reaktionsgleichung

Reaktionsgleichung von HRID 606800
C[Al](C)C.C(O[C:8](=[O:24])[C:9]1[CH:14]=[C:13]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[CH:12]=[N:11][CH:10]=1)C.[CH3:25][NH:26][O:27][CH3:28].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:23][C:19]1[CH:18]=[C:17]([C:16]#[C:15][C:13]2[CH:12]=[N:11][CH:10]=[C:9]([CH:14]=2)[C:8]([N:26]([O:27][CH3:28])[CH3:25])=[O:24])[CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 9357Potassium Sodium TartrateHCID 14232N,O-DimethylhydroxylamineHCID 16682925TrimethylaluminumHCID 670477625-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester

Produkt 1

HCID 86622467HCID 86622467, VerbindungAusbeute 33,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sequentially add a 2 M solution of trimethylaluminum in toluene (0.64 g, 8.91 mmol) and 5-(3-fluorophenylethynyl)-nicotinic acid ethyl ester (0.24 g, 0.89 mmol), (prepared essentially as described in PREPARATION 17), to a solution of N,O-dimethylhydroxylamine (0.435 g, 4.46 mmol) in anhydrous toluene (4.0 mL) at 0° C. After 30 min, warm to room temperature and stir overnight. Dilute the reaction with ethyl acetate and an aqueous saturated solution of Rochelle salt (potassium sodium tartrate) and stir vigorously for 1 h. Separate the organic layer; dry (magnesium sulfate), filter and concentrate. Purify the resulting residue by silica gel chromatography, eluting with a linear gradient of 100:0 to 60:40 tetrahydrofuran:hexanes, to give the title compound as a pale yellow oil (0.084 g, 33%).

Aufarbeitung

  1. custom(prepared essentially
  2. additionDilute
  3. customSeparate the organic layer
  4. dry with materialdry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the resulting residue by silica gel chromatography
  8. washeluting with a linear gradient of 100:0 to 60:40 tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-587fed56830847d1b4748c7a75299f09
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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