Sulfuric Acid → trans-4-Acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

HRID 231229

반응식

HRID 231229 반응식
[Si:1]([O:8][CH:9]([C@H:11]1[C@H:14]([C:15]#[C:16][Si](C)(C)C)[NH:13][C:12]1=[O:21])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:23].C(OCC)(=O)C>O1CCCC1.O.S([O-])([O-])(=O)=O.[Hg+2]>[C:15]([C@@H:14]1[NH:13][C:12](=[O:21])[C@H:11]1[CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH3:10])(=[O:23])[CH3:16]

참가 물질

7

반응물 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 67788757trans-3-[1-(Tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone

생성물 1

HCID 67789308trans-4-Acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

시약·촉매·용매 3

HCID 24544Mercuric sulfate촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

trans-3-[1-(tert-Butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone (1.2 g) is dissolved in a mixture of tetrahydrofuran (20 ml) and water (2 ml), and mercury sulfate (0.07 g) and concentrated sulfuric acid (catalytic amount) are added, followed by stirring at room temperature for 15 hours. The reaction mixture is poured into a mixture of ethyl acetate (150 ml) and water (100 ml) and the organic layer is separated, washed with aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to give 0.60 g of trans-4-acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone.

후처리

  1. additionare added
  2. customthe organic layer is separated
  3. washwashed with aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c725bba06420412bae3985d8dd3dcd1b
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845210

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