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

HRID 34283

Reaction equation

HRID 34283 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a1ba749831c44b25a7dff0e80eb65fee
Source dataset
uspto-grants-1988_08
Patent number
US04761408

Linked notes

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