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 397787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397787
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 86626146potassium carbonate THFLösungsmittel

Versuchsvorschrift

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-hydroxysuccimmlde 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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8a14b59c7209409eb115113d45598b3b
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610689B2

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