L-Tryptophan, N-[(4-methylphenyl)sulfonyl]- → (2S)-2-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-[[(2S)-3-(1H-indol-3-yl)-2-(p-tolylsulfonylamino)propanoyl]amino]hexanoic acid
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][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:38][C@H:39]([C:50](O)=[O:51])[CH2:40][C:41]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[NH:43][CH:42]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1>>[CH3:28][C:29]1[CH:30]=[CH:31][C:32]([S:35]([NH:38][C@H:39]([C:50]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]([N:6]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:2][CH:3]([CH3:5])[CH3:4])[C:13]([OH:15])=[O:14])=[O:51])[CH2:40][C:41]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[NH:43][CH:42]=2)(=[O:37])=[O:36])=[CH:33][CH:34]=1Participants
3
Procedure
The title compound was prepared from Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine hydrochloride (350 mg, 1.0 mmol, example 5, step C) as described in general procedure Bc using Nα-(4-methylbenzenesulfonyl)-L-tryptophan (335 mg, 1.1 mmol) which was prepared in step A of example 2. The final product was purified by preparative HPLC to yield 650 mg (90%) of Nα-(4-nitrobenzenesulfonyl)-Nα-isobutyl-Nε-[N′α-(4-methylbenzenesulfonyl)-L-tryptophanyl]-L-lysine The latter derivative (300 mg) was hydrogenolysed following the indications of general procedure E. Purification by HPLC gave the desired material (235 mg, 75%).
Workup
- customwas prepared in step A of example 2
- customThe final product was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-3b265e0b6330473ab3bba837ea3d1d1b
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06506786B2
Reaction notes
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