N-(2-Thienylsulfonyl)-L-phenylalanine → (2S)-2-[isobutyl-(4-nitrophenyl)sulfonyl-amino]-6-[[(2S)-3-phenyl-2-(2-thienylsulfonylamino)propanoyl]amino]hexanoic acid

HRID 396889Notes

Reaction equation

HRID 396889 reaction equation
Cl.[CH2:2]([N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[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].[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[S:33]([NH:36][C@H:37]([C:45]([OH:47])=[O:46])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=[O:35])=[O:34]>>[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:45]([C@@H:37]([NH:36][S:33]([C:29]1[S:28][CH:32]=[CH:31][CH:30]=1)(=[O:35])=[O:34])[CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:46])[CH3:5].[CH3:5][CH:3]([CH2:2][N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[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:45]([C@@H:37]([NH:36][S:33]([C:29]1[S:28][CH:32]=[CH:31][CH:30]=1)(=[O:34])=[O:35])[CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:47])[CH3:4]

Participants

4

Reactant 2

HCID 704092N-(2-Thienylsulfonyl)-L-phenylalanineHCID 69107784Nalpha-isobutyl-Nalpha-(4-nitrobenzenesulfonyl)-L-lysine hydrochloride

Product 2

HCID 508552(2S)-2-[isobutyl-(4-nitrophenyl)sulfonyl-amino]-6-[[(2S)-3-phenyl-2-(2-thienylsulfonylamino)propanoyl]amino]hexanoic acidYield 156.9%HCID 508569(2S)-2-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-[[(2S)-3-phenyl-2-(2-thienylsulfonylamino)propanoyl]amino]hexanoic acid

Procedure

The title compound was prepared from Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine hydrochloride (400 mg, 1.03 mmol, example 5, step C) as described in general procedure Bc using Nα-(2-thiophenesulfonyl)-L-phenylalanine (311 mg, 1.2 mmol) which was prepared in step A of example 24. The final product was purified by preparative HPLC to yield 550 mg (80%) of Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-Nε-[N′α-(2-thiophenesulfonyl)-L-phenylalanyl]-L-lysine. The latter derivative was hydrogenolysed following the indications of general procedure E. Purification by HPLC gave the desired material (400 mg, 65%).

Workup

  1. customwas prepared in step A of example 24
  2. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-cacc1e06ef424d6c96657336feaaad08
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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