m-Chloroperbenzoic acid → 4-Methylsulphinyl-1-(4-phenyl-2-oxobutyl)azetidin-2-one

HRID 1420525Notes

Reaction equation

HRID 1420525 reaction equation
[CH3:1][S:2][CH:3]1[N:6]([CH2:7][C:8](=[O:17])[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5](=[O:18])[CH2:4]1.ClC1C=CC=C(C(OO)=[O:27])C=1>ClCCl>[CH3:1][S:2]([CH:3]1[N:6]([CH2:7][C:8](=[O:17])[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:5](=[O:18])[CH2:4]1)=[O:27]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 187820304-Methylthio-1-(4-phenyl-2-oxobutyl)azetidin-2-one

Product 1

HCID 187819434-Methylsulphinyl-1-(4-phenyl-2-oxobutyl)azetidin-2-oneYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-methylthio-1-(4-phenyl-2-oxobutyl)azetidin-2-one (0.4 g, 1.5 mmol) in dichloromethane (40 ml) was cooled to -60° C. To this a solution of meta-chloroperbenzoic acid (m-CPBA, 0.52 g, 1.5 mmol) in dry dichloromethane (50 ml) was added dropwise over 10 minutes, maintaining the temperature between -50 and -60° C. The mixture was stirred at room temperature for 60 minutes, washed with dil. Na2SO3, dil. NaHCO3, H2O (×2) and dried (MgSO4). Evaporation under reduced pressure gave a residue which was purified by flash chromatography on silica gel using ethyl acetate then petroleum ether/ethyl acetate to give 4-methylsulphinyl-1-(4-phenyl-2-oxobutyl)azetidin-2-one as a waxy yellow solid (0.18 g, 43%). 1H NMR demonstrated that this was a 1:1 mixture of diastereoisomers.

Workup

  1. temperaturemaintaining the temperature between -50 and -60° C
  2. washwashed with dil. Na2SO3, dil. NaHCO3, H2O (×2)
  3. dry with materialdried (MgSO4)
  4. customEvaporation under reduced pressure
  5. customgave a residue which
  6. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-db811821072549efafceaf4a302a1f0c
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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