Dicyclohexylcarbodiimide → (S)-N-[2-(acetylthio)-1-oxo-3-phenylpropyl]-L-leucine, 1,1-dimethylethyl ester

HRID 1440075

Reaktionsgleichung

Reaktionsgleichung von HRID 1440075
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([S:19][C@@H:20]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:21]([OH:23])=O)(=[O:18])[CH3:17].[NH2:31][C@H:32]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35].O.OC1C2N=NNC=2C=CC=1>O1CCCC1>[C:16]([S:19][CH:20]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:21]([NH:31][C@H:32]([C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:23])(=[O:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 7022311tert-butyl (2S)-2-amino-4-methylpentanoateHCID 10176891(S)-2-acetylthio-3-phenylpropanoic acidHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 57146369(S)-N-[2-(acetylthio)-1-oxo-3-phenylpropyl]-L-leucine, 1,1-dimethylethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

This salt is converted to the free acid. Dicyclohexylcarbodiimide in tetrahydrofuran is added to a solution of (S)-2-acetylthio-3-phenylpropionic acid, (L)-leucine, 1,1-dimethylethyl ester, and hydroxybenzotriazole hydrate in tetrahydrofuran at -8° and the reaction mixture is stirred overnight warming to room temperature, and is then worked up according to the procedure of Example 37 to yield (S)-N-[2-(acetylthio)-1-oxo-3-phenylpropyl]-L-leucine, 1,1-dimethylethyl ester as a clear, light yellow, viscous oil.

Quellen und Nachweise

ORD-Eintrag
ord-03e7b494a8c846a99bdc2b5b95440cd0
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05496805

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