m-Chloroperbenzoic acid → HCID 22843866, compound

HRID 1196205Notes

Reaction equation

HRID 1196205 reaction equation
C1(S[C:8]([C@H:15]2[NH:18][C:17](=[O:19])[C@@H:16]2[C@H:20]([O:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[CH3:21])([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:9])C=CC=CC=1.ClC1C=CC=C(C(OO)=O)C=1>ClCCl.C1(C)C=CC=CC=1>[CH2:13]([O:12][C:10]([C:8]([C@H:15]1[NH:18][C:17](=[O:19])[C@@H:16]1[C@H:20]([O:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])[CH3:21])=[CH2:9])=[O:11])[CH3:14]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22841894HCID 22841894, compound

Product 1

HCID 22843866HCID 22843866, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of (3S,4S)-4-(1-phenylthio-1-ethoxycarbonylethyl)- 3-(1-(R)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone (2.0 g) in dry dichloromethane (50 ml) was treated with m-chloroperbenzoic acid (0.69 g) for 3 hours while ice-cooling. The reaction mixture was washed successively with a saturated sodium bicarbonate solution and brine, and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave an oily residue which was dissolved in toluene (18 ml). The toluene solution was stirred under reflux for 1 hour and concentrated in vacuo. An oily residue was purified by silica gel chromatography to yield (3S,4S)-4-(1-ethoxycarbonylethenyl)-3-(1-(R)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone.

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed successively with a saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationFiltration and concentration of the filtrate in vacuo
  5. customgave an oily residue which
  6. temperatureunder reflux for 1 hour
  7. concentrationconcentrated in vacuo
  8. customAn oily residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-56c6d46ee3c04484917677ecd89e50c9
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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