Ammonium → HCID 86740484, compound

HRID 653316Notes

Reaction equation

HRID 653316 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.[NH4+].[N+]([O-])([O-])=O.[Ce+4].[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

6

Reactant 3

HCID 223AmmoniumHCID 166767Nitric acid, cerium(4+) salt (4:1)HCID 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-3phthalimido-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-4dd67dd2caee4381805b10a618e067f7
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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