Sodium Sulfite → HCID 18781974, compound

HRID 1420532Notes

Reaction equation

[C:1]([S:5][CH:6]1[N:9]([CH2:10][C:11](=[O:20])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8](=[O:21])[CH2:7]1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:30])C=1.C(=O)([O-])O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[C:1]([S:5]([CH:6]1[N:9]([CH2:10][C:11](=[O:20])[CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8](=[O:21])[CH2:7]1)=[O:30])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -50 °C

Procedure

4-tert-Butylthio-1-(4-phenyl-2-oxobutyl)azetidin-2-one (0.6 g, 2 mmol) was dissolved in dry dichloromethane (30 ml) and the solution cooled to -50° C. A solution of m-CPBA (0.32 g, 2 mmol) in dry dichloromethane (20 ml) was added dropwise and the resulting mixture stirred for an additional 3 h. The mixture was poured into an aqueous solution of sodium hydrogen carbonate and sodium sulphite. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with sodium hydrogen carbonate solution, dried (MgSO4) and evaporated to give a solid which was purified by flash hromatography using ethyl acetate/ether and ethyl acetate as the eluting solvents. Evaporation of the appropriate fractions gave the title compound as a colourless solid, 0.3 g, 48%, m.p. 79-81° C.

Workup

customThe layers were separated
extractionthe aqueous layer was extracted with dichloromethane
washThe combined organic extracts were washed with sodium hydrogen carbonate solution
dry with materialdried (MgSO4)
customevaporated
customto give a solid which
customwas purified by flash hromatography
customEvaporation of the appropriate fractions

Sources & evidence

ORD record: ord-79864d0bc11849dfbd9a016e58f97819
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071899

Reaction notes

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