methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate → N-[3-(1-Naphthalenyl)-2-(1-naphthalenylmethyl)-1-oxopropyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine

Participants

Reaction Steps

In process analogous to Example H by substituting α-(1-naphthalenylmethyl)-1-naphthalenepropanoic acid (obtained by reacating di-tertiary-butylmalonate (one equivalent) with 1-chloromethylnaphthylene (two equivalents) and sodium hydride (two equivalents) followed by refluxing in acetic acid) for N-[(phenylmethoxy)carbonyl]-1-(triphenylmethyl)-L-histidine and Nε -carbobenzoxy-lysine, methyl ester for (3S)-3-amino-2-hydroxy-5-methylhexanoic acid, 1-methylethyl ester, monohydrochloride (mixture of isomers at hydroxy center) one obtains the methyl ester of the title compound which is then hydrolyzed with sodium hydroxide in aqueous methanol to afford the title compound.

Provenance & Evidence