Triethylamine → N-(t-butyldimethylsilyl)-3-azido 4-(2-trifluoroacetoxyethyl)-azetidin-2-one

HRID 1856065Notes

Reaction equation

HRID 1856065 reaction equation
C(N(CC)CC)C.[N:8]([CH:11]1[CH:14]([CH2:15][CH2:16][O:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[NH:13][C:12]1=[O:24])=[N+:9]=[N-:10].[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CN(C)C=O>[Si:25]([N:13]1[CH:14]([CH2:15][CH2:16][O:17][C:18](=[O:23])[C:19]([F:20])([F:21])[F:22])[CH:11]([N:8]=[N+:9]=[N-:10])[C:12]1=[O:24])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 543317643-Azido-4-(2-trifluoroacetoxyethyl)azetidin-2-one

Product 1

HCID 20563671N-(t-butyldimethylsilyl)-3-azido 4-(2-trifluoroacetoxyethyl)-azetidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.2 mol) is added dropwise to an ice-cold stirred solution of 3-azido-4-(2-trifluoroacetoxyethyl)-azetidin-2-one (0.2 mol) and t-butyldimethylsilyl chloride (0.2 mol) in dimethylformamide (100 ml). The resulting mixture is stirred for 10 min. in the cold and for 10 min at room temperature, and then evaporated under vacuum to remove DMF. The residue is taken up to methylene chloride, washed with water and brine, dried with magnesium sulfate, and evaporated under vacuum to provide N-(t-butyldimethylsilyl)-3-azido 4-(2-trifluoroacetoxyethyl)-azetidin-2-one.

Workup

  1. customevaporated under vacuum
  2. customto remove DMF
  3. washwashed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-938a84271ff64895b67121b56ff969dd
Source dataset
uspto-grants-1980_08
Patent number
US04217453

Reaction notes

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