Triethylamine → alpha,epsilon-dicarbobenzoxy-L-lysyl-L-phenylalanine benzyl ester
Reaktionsgleichung
[C:1]([C@@:11]([C:28](O)=[O:29])([CH2:13][CH2:14][CH2:15][CH:16]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[NH2:17])[NH2:12])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:46]([O:53][C:54](=[O:64])[C@H:55]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[NH2:56])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH2:46]([O:53][C:54](=[O:64])[C@H:55]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[NH:56][C:28](=[O:29])[C@:11]([C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])([CH2:13][CH2:14][CH2:15][CH:16]([C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[NH2:17])[NH2:12])[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1Komponenten
8
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirred solution of α,ε-dicarbobenzoxy-L-lysine (4) (96 mmol, 39.69 g), toluene (310 ml) and triethylamine (96 mmol, 9.70 g) at 0° C., was added, over a period of 15 minutes, iso-butyl chloroformate (109 mmol, 14.88 g), maintaining the temperature between -5° and 0° C. The resulting jelly-like reaction mixture was stirred for 30 minutes at 0° C. and then a slurry of L-phenylalanine benzyl ester, p-toluene sulphonate (1) (96 mmol, 40.99 g) in chloroform (470 ml) and triethylamine (96 mmol, 9.70 g) was added quickly in one portion and the clear solution was allowed to stir at ambient temperature overnight.
Aufarbeitung
- customThe resulting jelly-like reaction mixture
- stirringto stir at ambient temperature overnight
Quellen und Nachweise
- ORD-Eintrag
- ord-ac60421b493c45569276741815aa824e
- Quelldatensatz
- uspto-grants-1983_03
- Patentnummer
- US04376766
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