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

HRID 846470

Reaction equation

HRID 846470 reaction equation
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

Participants

4

Reactant 3

HCID 6994982methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoateHCID 13913909isopropyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoate hydrochlorideHCID 15545280Z-His(Trt)-OH

Product 1

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

Procedure

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.

Sources & evidence

ORD record
ord-6eb3dad8b6f74fb59c1c86d3db3d02d0
Source dataset
uspto-grants-1992_08
Patent number
US05135914

Linked notes

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