Ammonium cerium (IV) nitrate → (3R,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone

HRID 34283

Reaktionsgleichung

Reaktionsgleichung von HRID 34283
[N+]([O-])([O-])=O.[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.COC1C=CC(C[N:30]2[C@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@@H:32]([C@H:38]([O:40][C:41]([O:43][CH2:44][CH:45]=[CH2:46])=[O:42])[CH3:39])[C:31]2=[O:47])=CC=1>O.C(#N)C>[CH2:44]([O:43][C:41]([O:40][C@@H:38]([C@@H:32]1[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[NH:30][C:31]1=[O:47])[CH3:39])=[O:42])[CH:45]=[CH2:46]

Komponenten

5

Edukt 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 18604779(3R,4R)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone

Produkt 1

HCID 18604782(3R,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

At 10°, a solution of 5.37 g of cerium(IV) ammonium nitrate in 15 ml of water is added to a solution of 900 mg (1.18 mmol) of (3R,4R)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone in 30 ml of acetonitrile, and the whole is stirred for two hours at room temperature. After extraction with ethyl acetate, washing with saturated NaHCO3 solution, drying of the organic phase over sodium sulphate and concentration by evaporation under reduced pressure, the crude title compound, which is purified by chromatography over silica gel using toluene/ethyl acetate (4:1 and 1:1), is obtained.

Aufarbeitung

  1. extractionAfter extraction with ethyl acetate
  2. washwashing with saturated NaHCO3 solution
  3. dry with materialdrying of the organic phase over sodium sulphate and concentration by evaporation under reduced pressure
  4. customthe crude title compound, which is purified by chromatography over silica gel
  5. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-a1ba749831c44b25a7dff0e80eb65fee
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761408

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