Acetic Acid → HCID 77316455, compound

HRID 1494504Notes

Reaction equation

HRID 1494504 reaction equation
[CH2:1]([N:3]1[CH:6](SC2C=CC(C)=CC=2)[CH2:5][C:4]1=[O:15])[CH3:2].[C:16]([OH:19])(=[O:18])[CH3:17]>CCOCC.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([N:3]1[CH:6]([O:18][C:16](=[O:19])[CH3:17])[CH2:5][C:4]1=[O:15])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 131716916HCID 131716916, compound

Product 1

HCID 77316455HCID 77316455, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 351 mg (1 mmol) of (1'R, 3S, 4R)-3-(1'-tert-butyldimethylsililoxy)ethyl-4-p-methylphenylthio-2-azetidinone and 100 mg (0.5 mmol) of copper (II) acetate monohydrate in 2 ml of acetic acid was heated at 110° C. for 5 minutes with stirring. The reaction mixture was diluted with ether and the insoluble materials were filtered off. The filtrate was washed with saturated sodium bicarbonate solution and then water, dried, and concentrated to produce 223 mg (yield: 77.6%) of the title compound as white crystals.

Workup

  1. filtrationthe insoluble materials were filtered off
  2. washThe filtrate was washed with saturated sodium bicarbonate solution
  3. dry with materialwater, dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-856b26e674d1441ebe0e56a58d944b03
Source dataset
uspto-grants-1991_06
Patent number
US05026844

Reaction notes

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