Water → HCID 18781939, compound

HRID 1420537Notes

Reaction equation

HRID 1420537 reaction equation
O.[CH2:2]([NH:9][C:10](=[O:19])[CH2:11][N:12]1[CH:15]([S:16][CH3:17])[CH2:14][C:13]1=[O:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O:24]O)(C)(C)C>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH2:2]([NH:9][C:10](=[O:19])[CH2:11][N:12]1[CH:15]([S:16]([CH3:17])=[O:24])[CH2:14][C:13]1=[O:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6410tert-Butyl hydroperoxideHCID 18781961HCID 18781961, compound

Product 1

HCID 18781939HCID 18781939, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolvent2×

Procedure

4RSR-(-)-N-Benzyl-(4-methylsulphinyl-2-oxoazetidin-1-yl )acetamide A solution of S(-)1,1'-bi-2-napthol (0.012 g, 4.2 μmol) in toluene (2 ml) was treated with titanium isopropoxide (0.012 g, 21 μmol) in water (6 mg, 0.033 mmol). The resulting mixture was stirred at room temperature for 1 h. A solution of (-)-N-Benzyl (4-methylthio-2-oxoazetidin-1-yl)acetamide (0.2 g, 0.76 mmol) in toluene was added. After 30 mins t-butylhydroperoxide (136 mg, 1.5 mmol) was added and the mixture stirred for 3h. After evaporation to dryness, the residue was purified by flash chromatography on silica (EtOAc/EtOH 6:1 to 3:1) to give (-)-N-benzyl-(4-methylsulphinyl-2-oxoazetidin-1-yl)acetamide as a solid, 70 mg, 33% m.p. 138-140° C, [α]D25 =-237° (c=1.35, EtOH).

Workup

  1. stirringthe mixture stirred for 3h
  2. customAfter evaporation to dryness
  3. customthe residue was purified by flash chromatography on silica (EtOAc/EtOH 6:1 to 3:1)

Sources & evidence

ORD record
ord-2f028eecec654733ba47176a270e22aa
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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