Acetic Acid → N-(t-butyldimethylsilyl)-3-azido-4-(2-hydroxyethyl)-azetidin-2-one

HRID 1154913Notes

Reaction equation

HRID 1154913 reaction equation
C[O-].[Na+].[Si:4]([N:11]1[CH:14]([CH2:15][CH2:16][O:17]C(=O)C(F)(F)F)[CH:13]([N:24]=[N+:25]=[N-:26])[C:12]1=[O:27])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].C(O)(=O)C>CO>[Si:4]([N:11]1[CH:14]([CH2:15][CH2:16][OH:17])[CH:13]([N:24]=[N+:25]=[N-:26])[C:12]1=[O:27])([C:7]([CH3:9])([CH3:10])[CH3:8])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 20563671N-(t-butyldimethylsilyl)-3-azido 4-(2-trifluoroacetoxyethyl)-azetidin-2-one

Product 1

HCID 20563655N-(t-butyldimethylsilyl)-3-azido-4-(2-hydroxyethyl)-azetidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium methoxide (0.02 mol) in methanol (20 ml) is added to an ice-cold solution of N-(t-butyldimethylsilyl)-3-azido-4-(2-trifluoroacetoxyethyl)-azetidin-2-one (0.1 mol) in methanol (100 ml). After stirring in the cold for 10 min, the solution is treated with acetic acid (2 ml) and concentrated under vacuum. The resdue is taken up in ethyl acetate, washed with water, 5% sodium bicarbonate solution, and brine, dried, and evaporated. The residue is chromatographed on silica gel to give N-(t-butyldimethylsilyl)-3-azido-4-(2-hydroxyethyl)-azetidin-2-one.

Workup

  1. concentrationconcentrated under vacuum
  2. washwashed with water, 5% sodium bicarbonate solution, and brine
  3. customdried
  4. customevaporated
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-63fbdf8de5e24bf7909a251ca7590d60
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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