4-Methylmorpholine → HCID 54346309, Verbindung

HRID 437126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 437126
[C:1]([NH:4][C@H:5]([C:7]([NH:9][C@H:10]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=O)=[O:13])[CH3:11])=[O:8])[CH3:6])(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:37]([O:39][C:40](=[O:44])[N:41]([CH3:43])[NH2:42])[CH3:38]>O1CCCC1>[CH2:37]([O:39][C:40](=[O:44])[N:41]([CH3:43])[NH:42][C:16](=[O:18])[C@@H:15]1[CH2:19][CH2:20][CH2:21][N:14]1[C:12](=[O:13])[C@H:10]([CH3:11])[NH:9][C:7](=[O:8])[C@H:5]([CH3:6])[NH:4][C:1](=[O:3])[CH3:2])[CH3:38]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 11217246N-methylethoxycarbohydrazideHCID 12895631HCID 12895631, Verbindung

Produkt 1

HCID 54346309HCID 54346309, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of acetylalanylalanylproline (2 mmole) and N-methylmorpholine (2 mmole) in dry tetrahydrofuran (20 ml) at -20° to -25° C. is added isobutyl chloroformate (2 mmole). After 5 minutes a solution of 2-azaalanine ethyl ester (2 mmole) in tetrahydrofuran (3 ml) is added dropwise and the reaction mixture is allowed to warm to room temperature over a period of 1 hour and stirred for a further 4 hours. The precipitate is filtered off and the filtrate is evaporated to dryness. Chromatography on silica gel (50 gm) and elution with 10% methanol in chloroform gives pure acetylalanylalanylprolyl-2-azaalanine ethyl ester.

Aufarbeitung

  1. filtrationThe precipitate is filtered off
  2. customthe filtrate is evaporated to dryness
  3. washChromatography on silica gel (50 gm) and elution with 10% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-9162fa50c00149bab7ee6ef08bb200fa
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04029772

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