Toluene → N-(2,6-dichlorobenzoyl)-4-[2-[2-(methoxycarbonyl)ethenyl]phenyl]-L-phenylalanine methyl ester

HRID 24646

Reaktionsgleichung

Reaktionsgleichung von HRID 24646
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2C=O)=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].[CH3:32][O:33][C:34](=[O:55])[CH:35]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:56]1(C)C=CC=CC=1>>[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH:56]=[CH:35][C:34]([O:33][CH3:32])=[O:55])=[CH:21][CH:22]=1)[NH:5][C:6](=[O:15])[C:7]1[C:8]([Cl:14])=[CH:9][CH:10]=[CH:11][C:12]=1[Cl:13]

Komponenten

4

Edukt 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 54369932N-(2,6-Dichlorobenzoyl)-4-(2-formylphenyl)-L-phenylalanine methyl ester

Produkt 1

HCID 54296539N-(2,6-dichlorobenzoyl)-4-[2-[2-(methoxycarbonyl)ethenyl]phenyl]-L-phenylalanine methyl ester

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N-(2,6-Dichlorobenzoyl)-4-(2-formylphenyl)-L-phenylalanine methyl ester (51.7 mg) and (triphenylphosphoranylidene)acetic acid methyl ester (75.8 mg) were dissolved in anhydrous toluene (1 mL) and stirred at 80° C. under N2 for 18 h. The mixture was allowed to cool and purified by preparative TLC (silica gel) using hexanes/EtOAc (2:1) as eluent to give N-(2,6-dichlorobenzoyl)-4-[2-[2-(methoxycarbonyl)ethenyl]phenyl]-L-phenylalanine methyl ester (48.0 mg). ESMS: m/z 512 (MH+).

Aufarbeitung

  1. temperatureto cool
  2. custompurified by preparative TLC (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-07fe43342f9045cda61fb035156ecdbf
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855843B2

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