Potassium Persulfate → (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-one

HRID 2255667노트

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HRID 2255667 반응식
[Si:1]([O:8][C@@H:9]([C@@H:11]1[CH2:14][N:13](CC2C=CC(OC)=CC=2)[C:12]1=[O:24])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P([O-])([O-])(O)=O.[K+].[K+]>C(#N)C.O>[Si:1]([O:8][C@@H:9]([C@@H:11]1[CH2:14][NH:13][C:12]1=[O:24])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 24412Potassium PersulfateHCID 24450Potassium Phosphate, DibasicHCID 54758409(3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-(4-methoxybenzyl)azetidin-2-one

생성물 1

HCID 10130795(3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-one수율 44.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

A mixture of (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-(4-methoxybenzyl)azetidin-2-one (2.45 g), potassium persulfate (4.73 g) and dipotassium hydrogen phosphate (3.66 g) in acetonitrile (35 ml) and water (30 ml) was stirred at 70° C. for 2 hours. The mixture was evaporated and the residue was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water and an aqueous sodium chloride in turn, and then dried over magnesium sulfate. The resultant solution was evaporated and the residue was column-chromatographed on silica gel (eluent : a mixture of hexane and ethyl acetate, 3:1) to give (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-one (0.71 g).

후처리

  1. customThe mixture was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water
  4. dry with materialan aqueous sodium chloride in turn, and then dried over magnesium sulfate
  5. customThe resultant solution was evaporated
  6. customthe residue was column-chromatographed on silica gel (eluent
  7. additiona mixture of hexane and ethyl acetate, 3:1)

출처 및 근거

ORD 기록
ord-4658228a3c334de3b89d9514b0e19657
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05241064

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