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

Reaktionsgleichung

C1(COC(N[C@H](C(O)=O)CC2N=CN([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=CC=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)C3C=CC=CC=3)C=2)=O)C=CC=CC=1.[C:41]([NH:51][CH2:52][CH2:53][CH2:54][CH2:55][C@@H:56]([C:58]([O:60]C)=[O:59])[NH2:57])([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42].Cl.N[C@@H:64]([CH2:73][CH:74]([CH3:76])[CH3:75])[CH:65](O)[C:66]([O:68]C(C)C)=O>>[C:36]1([CH2:35][CH:65]([CH2:64][C:73]2[C:74]3[C:75](=[CH:27][CH:28]=[CH:29][CH:76]=3)[CH:32]=[CH:19][CH:26]=2)[C:66]([NH:57][C@H:56]([C:58]([OH:60])=[O:59])[CH2:55][CH2:54][CH2:53][CH2:52][NH:51][C:41]([O:43][CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:42])=[O:68])[C:27]2[C:26](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:19]=[CH:32][CH:37]=1

Komponenten

Edukt 3

HCID 6994982methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate

HCID 13913909isopropyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoate hydrochloride

HCID 15545280Z-His(Trt)-OH

Produkt 1

HCID 15177038N-[3-(1-Naphthalenyl)-2-(1-naphthalenylmethyl)-1-oxopropyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine

Versuchsvorschrift

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.