L-Tryptophan, N-[(4-methylphenyl)sulfonyl]- → methyl (2S)-6-[[(2S)-3-(1H-indol-3-yl)-2-(p-tolylsulfonylamino)propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoate

HRID 431333Notes

Reaction equation

HRID 431333 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[N:5]([CH2:16][CH:17]([CH3:19])[CH3:18])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:36][C@H:37]([C:48](O)=[O:49])[CH2:38][C:39]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[NH:41][CH:40]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C1COCC1.C([O-])([O-])=O.[K+].[K+].Cl>[CH3:26][C:27]1[CH:28]=[CH:29][C:30]([S:33]([NH:36][C@H:37]([C:48]([NH:24][CH2:23][CH2:22][CH2:21][CH2:20][C@H:4]([N:5]([S:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:16][CH:17]([CH3:18])[CH3:19])[C:3]([O:2][CH3:1])=[O:25])=[O:49])[CH2:38][C:39]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[NH:41][CH:40]=2)(=[O:35])=[O:34])=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 1190064L-Tryptophan, N-[(4-methylphenyl)sulfonyl]-HCID 22975548Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine methyl ester

Product 1

HCID 508592methyl (2S)-6-[[(2S)-3-(1H-indol-3-yl)-2-(p-tolylsulfonylamino)propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoateYield 71%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 86626146potassium carbonate THFSolvent

Procedure

To a stirred solution of Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine methyl ester (369 mg, 1 mmol, example 65, step C) in THF/K2CO3 (1M) (3 mL/3 mL) was added Nα-(4-methylbenzenesulfonyl)-L-tryptophan N-hydroxysuccininide ester (547 mg, 1.2 mmol). The reaction mixture was stirred overnight, then diluted with 1N HCl and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated. The crude was purified by flash chromatography using hexane/EtOAc as eluent to afford the desired product (71% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-16f07992e78b446c98f7049bf62e0899
Source dataset
uspto-grants-2003_12
Patent number
US06656965B2

Reaction notes

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