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

HRID 846470

反応式

HRID 846470 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

出典と根拠

ORDレコード
ord-6eb3dad8b6f74fb59c1c86d3db3d02d0
出典データセット
uspto-grants-1992_08
特許番号
US05135914

関連ノート

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