Reaktion #62561

ord-a1ba749831c44b25a7dff0e80eb65fee

Reaktionsgleichung

O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Ce+4].[NH4+]
cerium(IV) ammonium nitrate
C=CCOC(=O)O[C@H](C)[C@H]1C(=O)N(Cc2ccc(OC)cc2)[C@@H]1OC(C)=O
(3R,4R)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone
→
C=CCOC(=O)O[C@H](C)[C@H]1C(=O)N[C@@H]1OC(C)=O
(3R,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone

Edukte

O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Ce+4].[NH4+]
cerium(IV) ammonium nitrate
C=CCOC(=O)O[C@H](C)[C@H]1C(=O)N(Cc2ccc(OC)cc2)[C@@H]1OC(C)=O
(3R,4R)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone

Reagenzien

Keine

Lösungsmittel

O
water
CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    ExtraktionAfter extraction with ethyl acetate
  2. 2
    Waschenwashing with saturated NaHCO3 solution
  3. 3
    Trocknendrying of the organic phase over sodium sulphate and concentration by evaporation under reduced pressure
  4. 4
    Sonstigethe crude title compound, which is purified by chromatography over silica gel
  5. 5
    Sonstigeis obtained

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04761408uspto-grants-1988_08