Acetic Acid → 3-Azido-4-(2-hydroxyethyl)-2-azetidinone

HRID 2231604Notes

Reaction equation

HRID 2231604 reaction equation
C(O)(=O)C.CC1(C)[O:13][CH2:12][CH2:11][CH:10]2[N:7]1[C:8](=[O:17])[CH:9]2[N:14]=[N+:15]=[N-:16]>O>[N:14]([CH:9]1[CH:10]([CH2:11][CH2:12][OH:13])[NH:7][C:8]1=[O:17])=[N+:15]=[N-:16]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 12769232HCID 12769232, compound

Product 1

HCID 155923893-Azido-4-(2-hydroxyethyl)-2-azetidinoneYield 22.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 8 ml of acetic acid and 2 ml of water is added 1.0 g of 2,2-dimethyl-7-azido-1-aza-3-oxa-bicyclo[4,2,0]octane-8-one (1:4 cis-trans mixture) and the mixture is stirred at 60° C. for 4 hours and concentrated to dryness. Tetrahydrofuran (15 ml) is added and the insoluble matter is filtered off. The filtrate is concentrated to dryness and the residue is dissolved in a small amount of chloroform and subjected to column chromatography using silica gel (20 g), elution being carried out with chloroform-ethyl acetate (1:1) and ethyl acetate in that order to give 179 mg of 3-azido-4-hydroxyethyl-2-azetidinone as a colorless oil.

Workup

  1. concentrationconcentrated to dryness
  2. additionTetrahydrofuran (15 ml) is added
  3. filtrationthe insoluble matter is filtered off
  4. concentrationThe filtrate is concentrated to dryness
  5. dissolutionthe residue is dissolved in a small amount of chloroform
  6. washsilica gel (20 g), elution

Sources & evidence

ORD record
ord-100020ca0380470eb6c45d8fb1a50d4f
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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