m-Chloroperbenzoic acid → 1-Acetyl-4-methylsulfinylazetidine-2-one

HRID 484036Notes

Reaction equation

HRID 484036 reaction equation
[C:1]([N:4]1[CH:7]([S:8][CH3:9])[CH2:6][C:5]1=[O:10])(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)Cl>[C:1]([N:4]1[CH:7]([S:8]([CH3:9])=[O:19])[CH2:6][C:5]1=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 145437851-Acetyl-4-(methylthio)azetidin-2-one

Product 1

HCID 197488041-Acetyl-4-methylsulfinylazetidine-2-oneYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 130 mg (0.82 mM) N-acetyl-4-methylthioazetidinone and 200 mg (0.93 mM) 80% m-chloroperbenzoic acid in 5 ml methylene chloride was stirred at room temperature 5 minutes. After removing the solvent in vacuo. The residue was chromatographed on 2-2000μ silica gel plates in hexane/ethyl acetate to yield 57 mg (40%) of 1-acetyl-4-methylsulfinylazetidine-2-one.

Workup

  1. customAfter removing the solvent in vacuo
  2. customThe residue was chromatographed on 2-2000μ silica gel plates in hexane/ethyl acetate

Sources & evidence

ORD record
ord-5fe8b7b8e9a7474aa41348662e14d615
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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