Water → HCID 54529752, compound

HRID 2166286Notes

Reaction equation

HRID 2166286 reaction equation
C(C(CC1C=CC(OC)=CC=1)[N:11]1[CH:14]([CH2:15][C:16](=[O:33])[C:17]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)=[O:21])=[N+:18]=[N-:19])[CH:13]([CH:34]([O:36][C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=2)=[O:38])[CH3:35])[C:12]1=[O:50])C1C=CC(OC)=CC=1.O>C(#N)C.O>[N+:47]([C:44]1[CH:43]=[CH:42][C:41]([CH2:40][O:39][C:37]([O:36][CH:34]([CH:13]2[CH:14]([CH2:15][C:16](=[O:33])[C:17]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)=[O:21])=[N+:18]=[N-:19])[NH:11][C:12]2=[O:50])[CH3:35])=[O:38])=[CH:46][CH:45]=1)([O-:49])=[O:48]

Participants

4

Reactant 2

HCID 962WaterHCID 57278972HCID 57278972, compound

Product 1

HCID 54529752HCID 54529752, compound

Reagents, catalysts & solvents 1

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

Procedure

1.27 g 1-(di-p-anisylmethyl)-3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-[3-(p-nitrobenzyloxycarbonyl)-2-oxo-3-diazopropyl]-2-azetidinone was dissolved in 50 ml of acetonitrile-water (9:1 by volume), and 2.7 g of ceric ammonium nitrate was added thereto all at once under ice-cooling. After vigorously stirring, the mixture was further stirred at room temperature for 30 minutes. Cool water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel chromatography to obtain 3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-[3-(p-nitrobenzyloxycarbonyl)-2-oxo-3-diazopropyl]-2-azetidinone.

Workup

  1. temperatureall at once under ice-cooling
  2. stirringthe mixture was further stirred at room temperature for 30 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e839b9e2981547859278141f9ee92e14
Source dataset
uspto-grants-1990_07
Patent number
US04943569

Reaction notes

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