4-Methylmorpholine → Nalpha [S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteinyl]-Nepsilon-t-butoxycarbonyl-L-lysine methyl ester

HRID 249571

Reaktionsgleichung

Reaktionsgleichung von HRID 249571
[CH2:1]([S:8][CH2:9][C@@H:10]([C:26](O)=[O:27])[NH:11][C:12](=[O:25])[C:13]([CH3:24])([CH3:23])[CH2:14][S:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][O:30][C:31](=[O:46])[C@H:32]([CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH2:33].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.C1C=CC=CC=1.C(OCC)(=O)C>[CH3:29][O:30][C:31](=[O:46])[C@H:32]([CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[O:40])[NH:33][C:26](=[O:27])[C@H:10]([CH2:9][S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[NH:11][C:12](=[O:25])[C:13]([CH3:24])([CH3:23])[CH2:14][S:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

9

Edukt 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7018776(S)-Methyl 2-amino-6-((tert-butoxycarbonyl)amino)hexanoateHCID 14969990S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteine

Produkt 1

HCID 86746877Nalpha [S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteinyl]-Nepsilon-t-butoxycarbonyl-L-lysine methyl esterAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteine (4.01 g), Nε -t-butoxycarbonyl-L-lysine methyl ester (2.08 g) and NMM (1.1 ml) in DMF (20 ml), HOBt (2.16 g) and then a solution of DCC (1.82 g) in DMF (10 ml) were added slowly under ice cooling. The mixture was stirred for 1 hr. under ice cooling and for 18 hr. at room temperature. After an addition of a mixture of ethyl acetate and benzene (2:1, 500 ml), the mixture was washed with 10% citric acid solution, water, saturated sodium bicarbonate solution, water and then saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 3.22 g (61%) of the titled compound.

Aufarbeitung

  1. waitunder ice cooling and for 18 hr
  2. customat room temperature
  3. washthe mixture was washed with 10% citric acid solution, water, saturated sodium bicarbonate solution, water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-16f92afb86334198936b5dba7e08f801
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05214181

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