Acetic Acid → HCID 13619047, compound

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

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.