Water → 1-(t-Butyldimethylsilyl)-3-acetyl-4-(2'-hydroxyethyl)-2-azetidinone

HRID 345257Notes

Reaction equation

HRID 345257 reaction equation
C([N-][CH:5]([CH3:7])C)(C)C.[Li+].[Si:9]([N:16]1[CH:19]([CH2:20][CH2:21][O:22]C(=O)C)[CH2:18][C:17]1=[O:26])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[OH2:27].[Cl-].[Na+]>O1CCCC1>[Si:9]([N:16]1[CH:19]([CH2:20][CH2:21][OH:22])[CH:18]([C:5](=[O:27])[CH3:7])[C:17]1=[O:26])([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 2724682Lithium diisopropylamideHCID 13051149N-(t-butyldimethylsilyl)-4-(2-acetoxyethyl)azetidin-2-one

Product 1

HCID 143290001-(t-Butyldimethylsilyl)-3-acetyl-4-(2'-hydroxyethyl)-2-azetidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.1 equivalents of freshly prepared lithium diisopropylamide in 3 ml anhydrous tetrahydrofuran under a nitrogen atmosphere at -78° is added a solution of 1-(t-butyldimethylsilyl)-4-(2'-acetoxyethyl)-2-azetidinone (61 mg, 0.225 mmole) in 1 ml anhydrous tetrahydrofuran which has been cooled to -78°. After 12 minutes the reaction mixture is poured into 5 ml water. The solution is saturated with sodium chloride and extracted with methylene chloride. The combined methylene chloride solutions are washed with brine, dried over magnesium sulfate and filtered. Evaporation of the filtrate under reduced pressure gives 50 mg of crude product. Purification by preparative thick-layer chromatography on silica gel developing with ethyl acetate gives 1-(t-butyldimethylsilyl)-3-acetyl-4-(2'-hydroxyethyl)-2-azetidinone (19 mg).

Workup

  1. temperaturehas been cooled to -78°
  2. extractionextracted with methylene chloride
  3. washThe combined methylene chloride solutions are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customEvaporation of the filtrate under reduced pressure
  7. customgives 50 mg of crude product
  8. customPurification by preparative thick-layer chromatography on silica gel developing with ethyl acetate

Sources & evidence

ORD record
ord-19561103e519463bb4dacfd76cbbf11d
Source dataset
uspto-grants-1991_10
Patent number
US05055573

Reaction notes

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