Nalpha-isobutyl-Nalpha-(4-nitrobenzenesulfonyl)-L-lysine hydrochloride → (2S)-2-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-[[(2S)-2-[[2-(4-methoxyphenyl)acetyl]amino]-3-phenyl-propanoyl]amino]hexanoic acid

HRID 397804Notes

Reaction equation

HRID 397804 reaction equation
Cl.[CH2:2]([N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH:3]([CH3:5])[CH3:4].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([NH:39][C@H:40]([C:48](O)=[O:49])[CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:38])=[CH:32][CH:31]=1>>[CH3:4][CH:3]([CH2:2][N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:48]([C@@H:40]([NH:39][C:37]([CH2:36][C:33]1[CH:34]=[CH:35][C:30]([O:29][CH3:28])=[CH:31][CH:32]=1)=[O:38])[CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:49])[CH3:5]

Participants

3

Reactant 2

HCID 69107784Nalpha-isobutyl-Nalpha-(4-nitrobenzenesulfonyl)-L-lysine hydrochlorideHCID 69347446Nalpha-(4-methoxyphenylacetyl)-L-phenylalanine

Product 1

HCID 508685(2S)-2-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-[[(2S)-2-[[2-(4-methoxyphenyl)acetyl]amino]-3-phenyl-propanoyl]amino]hexanoic acid

Procedure

The title compound was prepared from Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine hydrochloride (200 mg, 0.45 mmol, example 5, step C) as described in general procedure Bc using Nα-(4-methoxyphenylacetyl)-L-phenylalanine (example 132, step A). The final product, Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-Nε-[N′α-(4-methoxyphenylacetyl)-L-phenylalanyl]-L-lysine was subsequently hydrogenolysed following the indications of general procedure E. Purification by HPLC gave the desired material (7 mg, 4%).

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-6244e887648244baa5ae59401c3274be
Source dataset
uspto-grants-2003_08
Patent number
US06610689B2

Reaction notes

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