HCID 131715510, compound → HCID 15573252, compound

HRID 1252204Notes

Reaction equation

HRID 1252204 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][O:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:17]([O:20][CH:21]1[NH:24][C:23](=[O:25])[CH2:22]1)(=[O:19])[CH3:18]>O.C(#N)C.O>[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][O:9][C:10]([O:12][CH:13]([CH:22]2[CH:21]([O:20][C:17](=[O:19])[CH3:18])[NH:24][C:23]2=[O:25])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 131715510HCID 131715510, compound

Product 1

HCID 15573252HCID 15573252, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Ceric ammonium nitrate (12.1 g) was added to the solution of 1-(di-p-anisylmethyl)-3-(1-p-nitrobenzyloxycarbonyloxyethane-4-acetoxy-2-azetidinone (6.06 g) in 10% H2O-acetonitrile (90 ml) in portions over 1 hour at room temperature, followed by stirring for 30 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and evaporated to give an oily residue which was then purified by silica gel chromatography to give 3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-acetoxy-2-azetidinone.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto give an oily residue which
  6. customwas then purified by silica gel chromatography

Sources & evidence

ORD record
ord-62b0db070bc34bb28180b105aef21cfe
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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