StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium hydride → N-[4-(t-butyloxycarbonyl)aminomethylbenzoyl]-4-benzyloxy-L-phenylalanine cyclohexylamide

HRID 330438
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 330438
C[CH:2]1[CH:7](C)[CH2:6][CH2:5][CH:4]([NH:9][C:10](=[O:45])[C@H:11]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:33][CH:32]=2)[NH:12][C:13](=[O:29])[C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:16][CH:15]=2)[CH2:3]1.[H-].[Na+].N1C=CC(CCl)=CC=1>CN(C)C=O>[CH:4]1([NH:9][C:10](=[O:45])[C@H:11]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:33][CH:32]=2)[NH:12][C:13](=[O:29])[C:14]2[CH:15]=[CH:16][C:17]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[CH:18][CH:19]=2)[CH2:5][CH2:6][CH2:7][CH2:2][CH2:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 745714-(Chloromethyl)pyridineHCID 54354000N-[4-(t-butyloxycarbonyl)aminomethylbenzoyl]-4-benzyloxy-L-phenylalanine 3,4-dimethylcyclohexylamide

Produkt 1

HCID 53735669N-[4-(t-butyloxycarbonyl)aminomethylbenzoyl]-4-benzyloxy-L-phenylalanine cyclohexylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

A mixture of the above compound (II) (1.70 g), palladium black (0.20 g), cyclohexene (6 ml), and ethanol (50 ml) was reacted under reflux of ethanol. After cooling, the solid was filtered off and the filtrate was concentrated to obtain N-(t-butyloxycarbonyl)-4-hydroxy-L-phenylalanine 4-pipecolylamide (III) (1.36 g). The compound (III) was dissolved, without purification, in N,N-dimethylformamide (20 ml). To this solution was added oily sodium hydride (60% content) (0.16 g), followed by stirring at room temperature for 30 minutes. To this solution was added a solution of 4-picolyl chloride (0.50 g) in N,N-dimethylformamide (5 ml) and the reaction was carried out at room temperature for 7 hours. Ice water was added to the reaction mixture and the resultant oily proudct was extracted with ethyl acetate. After a conventional post-treatment, N-(t-butyloxycarbonyl)-4-(4-picolyloxy)-L-phenylalanine 4-pipecolylamide (IV) (1.20 g) was obtained. From the compound (IV), N-(trans-4-aminomethylcyclohexylcarbonyl)-4-(4-picolyloxy)-L-phenylalanine-4-pipecolylamide (0.85 g) following the procedure of Example 6.

Aufarbeitung

  1. waitthe reaction was carried out at room temperature for 7 hours
  2. extractionthe resultant oily proudct was extracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-728e9c92fc304127a600243bf1863c65
Quelldatensatz
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04895842

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion