Potassium Persulfate → (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-one

HRID 2255667Notes

Reaction equation

[Si:1]([O:8][C@@H:9]([C@@H:11]1[CH2:14][N:13](CC2C=CC(OC)=CC=2)[C:12]1=[O:24])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P([O-])([O-])(O)=O.[K+].[K+]>C(#N)C.O>[Si:1]([O:8][C@@H:9]([C@@H:11]1[CH2:14][NH:13][C:12]1=[O:24])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-(4-methoxybenzyl)azetidin-2-one (2.45 g), potassium persulfate (4.73 g) and dipotassium hydrogen phosphate (3.66 g) in acetonitrile (35 ml) and water (30 ml) was stirred at 70° C. for 2 hours. The mixture was evaporated and the residue was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water and an aqueous sodium chloride in turn, and then dried over magnesium sulfate. The resultant solution was evaporated and the residue was column-chromatographed on silica gel (eluent : a mixture of hexane and ethyl acetate, 3:1) to give (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-one (0.71 g).

Workup

customThe mixture was evaporated
extractionthe residue was extracted with ethyl acetate
washThe extract was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water
dry with materialan aqueous sodium chloride in turn, and then dried over magnesium sulfate
customThe resultant solution was evaporated
customthe residue was column-chromatographed on silica gel (eluent
additiona mixture of hexane and ethyl acetate, 3:1)

Sources & evidence

ORD record: ord-4658228a3c334de3b89d9514b0e19657
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05241064

Reaction notes

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