Imidazole → Cis-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone

HRID 231226Notes

Reaction equation

HRID 231226 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][C@@H:15]([C@H:17]1[C@@H:20]([C:21]#[C:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[NH:19][C:18]1=[O:27])[CH3:16].C(OCC)(=O)C>CN(C)C=O.O>[Si:6]([O:14][C@@H:15]([C@H:17]1[C@@H:20]([C:21]#[C:22][Si:23]([CH3:24])([CH3:26])[CH3:25])[NH:19][C:18]1=[O:27])[CH3:16])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 18633014cis-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone

Product 1

HCID 57192380Cis-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Imidazole (0.2 g) and tert-butyldimethylsilyl chloride (0.3 g) are added to a solution of cis-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone (0.2 g) in N,N-dimethylformamide (7 ml), and the mixture is stirred at 60° C.-65° C. for 1.5 hours and then poured into a mixture of ethyl acetate (50 ml) and water (50 ml). The organic layer is separated, washed with aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure, and the residue is subjected to silica gel column chromatography to give cis i.e. (3R,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone as crystals. (0.24 g).

Workup

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

Sources & evidence

ORD record
ord-586969dc0b404a85ae55df1b08114d05
Source dataset
uspto-grants-1989_07
Patent number
US04845210

Reaction notes

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