Water → HCID 13336393, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 17.75 g of the product of Step B, 31 g of potassium peroxodisulfate, 110 ml of water and 160 ml of acetic acid was heated for 25 minutes with strong agitation in an oil bath at 120° C. and was then cooled to room temperature. 50 g of dipotassium phosphate were added to the mixture to adjust the pH to neutrality and was evaporated to dryness under reduced pressure. 250 ml of water and 150 ml of ethyl acetate were added to the residue and after stirring, sodium bicarbonate was added in small quantities until evolution of gas ceased. The mixture was filtered and the filtrate was rinsed with ethyl acetate. The decanted aqueous phase was re-extracted with 50 ml of ethyl acetate and the combined organic phases were dried, filtered, rinsed and evaporated to dryness under reduced pressure. The residue was chromatographed over 200 g of silica gel and eluted with methylene chloride with 25% of ethyl acetate. The rich fractions were recovered and evaporated to dryness. The residue was dissolved in ether, and the solution was rinsed and dried to obtain 5.4 g of cis 3-phthalimido-4-chloromethyl-2-azetidinone.

Provenance & Evidence