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

HRID 231229

Reaction equation

HRID 231229 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24544Mercuric sulfateCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c725bba06420412bae3985d8dd3dcd1b
Source dataset
uspto-grants-1989_07
Patent number
US04845210

Linked notes

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