Acetic Acid → HCID 66653131, compound

Participants

Reaction Steps

According to scheme VIII, ethylenediamine is first treated with an excess of benzyl chloroformate followed by mono-hydrolysis using hydrochloric acid in glacial acetic acid giving N-carboxybenzylethylenediamine 25 which is treated with N-acetyl-β-alanine methyl ester 5, giving the protected carbamate [2-[[-(acetylamino)-1-oxopropyl]amino]ethyl]carbamic acid, phenylmethyl ester 26 which is deprotected using palladium on carbon in refluxing ethanol/cyclohexane, giving amine 3-(acetylamino)-N-(2-aminoethyl)propanamide 27. Amine 27 is reacted with oleoyl chloride 1 to give the amide isostere product N-[2-[[3-(acetylamino)-1-oxopropyl]amino]ethyl]-9(Z)-octadecenamide 28. ##STR16##

Provenance & Evidence