Water → 3-Azido-4-(2-hydroxyethyl)-2-azetidinone

HRID 1154910Notes

Reaction equation

HRID 1154910 reaction equation
[N:1]([CH:4]1[C:11](=[O:12])[N:10]2[CH:5]1[CH2:6][CH2:7][O:8]C2(C)C)=[N+:2]=[N-:3].O>FC(F)(F)C(O)=O>[N:1]([CH:4]1[CH:5]([CH2:6][CH2:7][OH:8])[NH:10][C:11]1=[O:12])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 962WaterHCID 12769232HCID 12769232, compound

Product 1

HCID 155923893-Azido-4-(2-hydroxyethyl)-2-azetidinone

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7-Azido-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]-octane (0.2 mol) is dissolved in 2:1 trifluoroacetic acid --H2O (200 ml) and the solution is kept at room temperature (25° C.) for 10 minutes. The solution is concentration under vacuum to a syrup which is taken up in ethylacetate, washed with 5% sodium bicarbonate and brine, dried with sodium sulfate, and filtered. Evaporation of the solvent provides 3-azido-4-(2-hydroxyethyl)-azetidin-2-one.

Workup

  1. customis kept at room temperature
  2. custom(25° C.)
  3. customfor 10 minutes
  4. concentrationconcentration under vacuum to a syrup which
  5. washwashed with 5% sodium bicarbonate and brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e2d1f96963d74dc2b7254093e9049b3d
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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