N-carbobenzyloxyalanine → HCID 67788511, Verbindung
Reaktionsgleichung
[NH:1]1[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][CH:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:15]([O:22][C:23]([NH:25][C@H:26]([C:28](O)=[O:29])[CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)(=O)C>[CH2:15]([O:22][C:23]([NH:25][C@H:26]([C:28]([N:1]1[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][C@@H:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:29])[CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 10.0 g of ethyl octahydroindole-2-carboxylate (prepared in as shown in paragraph A of this example) in 400 ml of ethyl acetate add 17.0 g of N-benzyloxycarbonyl-(S)-alanine, N-hydroxysuccinimide ester. Stir the reaction mixture at room temperature for 20 hours and concentrate it in vacuo. Place the residue on a column of silica gel (3000 g, 60-200 mesh) and elute with chloroform:ethyl acetate 10:1 to give 1-[N-benzyloxycarbonyl-(S)-alanyl]octahydroindole-2(R)-carboxylic acid, ethyl ester, a colorless oil [α]D26 +22.0° (ethanol) and 1-[N-benzyloxycarbonyl-(S)alanyl]octahydroindole-2(S)-carboxylic acid, ethyl ester, a colorless oil [α]D26 -96.4° (ethanol).