Acetic Acid → HCID 13619047, compound

HRID 482826Notes

Reaction equation

HRID 482826 reaction equation
C([O:4][CH2:5][CH2:6][CH:7]1[NH:10][C:9](=[O:11])[CH:8]1[CH2:12][CH3:13])(=O)C.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CO>[CH2:12]([CH:8]1[CH:7]([CH2:6][CH2:5][OH:4])[NH:10][C:9]1=[O:11])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 20243488HCID 20243488, compound

Product 1

HCID 13619047HCID 13619047, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude 4-[2-(acetyloxy)ethyl]-3-ethyl-2-azetidinone is stirred with 9.7 g of potassium carbonate in 880 ml of absolute methanol at room temperature for 30 minutes. The mixture is neutralized with acetic acid and then evaporated to dryness at 50° C. under vacuum. The residue is suspended in a saturated aqueous solution of sodium chloride and the mixture is extracted with four 150-ml portions of ethyl acetate. The combined organic layers are dried over MgSO4 and then evaporated to dryness yielding 34 g of 3-ethyl-4-[2-(hydroxy)ethyl]-2-azetidinone which contains 80% of the trans isomer (estimated by N.M.R.). The I.R. and N.M.R. data confirm the assigned structure.

Workup

  1. customevaporated to dryness at 50° C. under vacuum
  2. extractionthe mixture is extracted with four 150-ml portions of ethyl acetate
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b2a6e42801f2474082f98cf6a0fed8da
Source dataset
uspto-grants-1986_03
Patent number
US04576746

Reaction notes

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