m-Chloroperbenzoic acid → HCID 18781944, compound

HRID 1420529Notes

Reaction equation

HRID 1420529 reaction equation
[CH3:1][S:2][CH:3]1[N:6]([CH2:7][C:8](=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5](=[O:23])[CH2:4]1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1>ClCCl>[CH3:1][S:2]([CH:3]1[N:6]([CH2:7][C:8](=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:5](=[O:23])[CH2:4]1)=[O:32]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18781937HCID 18781937, compound

Product 1

HCID 18781944HCID 18781944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-methylthio-1-(9-phenyl-2-oxononyl)azetidin-2-one (0.993 g, 2.98 mmol) in dry dichloromethane (90 ml) was cooled to -50° C. and mCPBA (0.95 g, 2.58 mmol) in dry dichloromethane (50 ml) was added dropwise over 30 minutes, then stirred for 90 minutes at room temperature. This was washed with dil Na2SO3, dil NaHCO3 and water (×2), dried (MgSO4)and evaporated to a solid (1.09 g). This was purified by flash chromatography on silica gel eluted with petroleum ether/ethyl acetate 1 ethanol to give 4-methylsulphinyl-1-(9-phenyl-2-oxononyl)azetidin-2-one (Example 5) as a white waxy solid (0.718 g, 69%).

Workup

  1. washThis was washed with dil Na2SO3, dil NaHCO3 and water (×2), dried (MgSO4)and
  2. customevaporated to a solid (1.09 g)
  3. customThis was purified by flash chromatography on silica gel
  4. washeluted with petroleum ether/ethyl acetate 1 ethanol

Sources & evidence

ORD record
ord-9988e34f8a344c528e34cc6ca67199b3
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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