Ammonium cerium (IV) nitrate → HCID 86740484, compound

HRID 465265Notes

Reaction equation

HRID 465265 reaction equation
[C:1]1(=[O:32])[N:5]([C@H:6]2[C@@H:9](/[CH:10]=[CH:11]/[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8](C3C=CC(OC)=CC=3)[C:7]2=[O:26])[C:4](=[O:27])[C:3]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:2]12.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>O1CCCC1.O>[C:4]1(=[O:27])[N:5]([C@H:6]2[C@@H:9](/[CH:10]=[CH:11]/[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:8][C:7]2=[O:26])[C:1](=[O:32])[C:2]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:3]12

Participants

5

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 10971934HCID 10971934, compound

Product 1

HCID 86740484HCID 86740484, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 25 ml of tetrahydrofuran is dissolved 1 g of cis-3-phthalimido-4-(E)-styryl-1-(p-methoxyphenyl)-2-oxoazetidine and under stirring at -5° C. to -10° C., solution of ammonium cerium (IV) nitrate (3 g) in 10 ml of water is added dropwise over a period of 5 minutes. Then, the mixture is stirred at -5° C. to 0° C. for 20 minutes. The tetrahydrofuran is distilled off under reduced pressure and the residue is shaken with ethyl acetate and water. The ethyl acetate layer is taken, washed with aqueous sodium sulfite and aqueous sodium chloride in this order and dried over anhydrous sodium sulfate. The solvent is then distilled off and the residue is purified by silica gel column chromatography [eluent: chloroform-ethyl acetate (7:3)] and crystallized from ethyl acetate-ether to give cis-3-phthalimido-4-(E)-styryl-2-oxoazetidine, melting at 168°-170° C.

Workup

  1. stirringThen, the mixture is stirred at -5° C. to 0° C. for 20 minutes
  2. distillationThe tetrahydrofuran is distilled off under reduced pressure
  3. stirringthe residue is shaken with ethyl acetate and water
  4. washwashed with aqueous sodium sulfite and aqueous sodium chloride in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is then distilled off
  7. customthe residue is purified by silica gel column chromatography [eluent: chloroform-ethyl acetate (7:3)]
  8. customcrystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-49d73b670cad4f0099b6134f58432b92
Source dataset
uspto-grants-1985_10
Patent number
US04550105

Reaction notes

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