Nalpha(4-nitrobenzenesulfonyl)-L-tryptophan → (2S)-6-[[(2S)-3-(1H-indol-3-yl)-2-[(4-nitrophenyl)sulfonylamino]propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 396877Notes

Reaction equation

HRID 396877 reaction equation
[CH2:1]([N:5]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:2]([CH3:4])[CH3:3].[N+:25]([C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:37][C@H:38]([C:49](O)=[O:50])[CH2:39][C:40]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[NH:42][CH:41]=2)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([O-:27])=[O:26]>>[CH3:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([N:5]([C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:49]([C@@H:38]([NH:37][S:34]([C:31]2[CH:32]=[CH:33][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=2)(=[O:35])=[O:36])[CH2:39][C:40]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[NH:42][CH:41]=2)=[O:50])[CH2:1][CH:2]([CH3:3])[CH3:4])(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 1572095Nalpha(4-nitrobenzenesulfonyl)-L-tryptophanHCID 23552860Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine

Product 1

HCID 508531(2S)-6-[[(2S)-3-(1H-indol-3-yl)-2-[(4-nitrophenyl)sulfonylamino]propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Procedure

The title compound was prepared from Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine (100 mg, 0.29 mmol, example 1, step E) as described in general procedure Bc using Nα-(4-nitrobenzenesulfonyl)-L-tryptophan (120 mg, 0.3 mmol) which was prepared in step A of example 5. The final product was purified by HPLC to give 66 mg (36%) of pure adduct.

Workup

  1. customwas prepared in step A of example 5
  2. customThe final product was purified by HPLC

Sources & evidence

ORD record
ord-3949c58a930745f485f54c833d31de10
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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