Triacetoxyperiodinane → HCID 59167774, Verbindung

HRID 1443652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443652
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25](=[O:44])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](=[O:43])[NH:33][CH2:34][CH:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[CH3:23][O:24][C:25](=[O:44])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](=[O:43])[NH:33][CH2:34][C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 57495437HCID 57495437, Verbindung

Produkt 1

HCID 59167774HCID 59167774, VerbindungAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add Dess-Martin periodinane (16.5 g, 38.7 mmol) to a solution of 7-(2-hydroxy-2-phenylethylcarbamoyl)heptanoic acid methyl ester (10.2 g, 33.3 mmol) in methylene chloride (360 mL) at 0° C. under nitrogen, stir and warm the mixture to room temperature for 4 hours. Filter the mixture through Celite, wash with ethyl acetate (3×100 mL) and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with hexane/ethyl acetate (60:40), to provide 7-(2-oxo-2-phenylethylcarbamoyl)heptanoic acid methyl ester (7.33 g, 72%).

Aufarbeitung

  1. filtrationFilter the mixture through Celite
  2. washwash with ethyl acetate (3×100 mL)
  3. customremove the solvent under reduced pressure
  4. customPurify the residue by flash column chromatography on silica gel
  5. washeluting with hexane/ethyl acetate (60:40)

Quellen und Nachweise

ORD-Eintrag
ord-cdbfac969faa48688099424f214ec448
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662771B2

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