(2-BOC-aminophenyl)boronic acid → N-(2,6-dichlorobenzoyl)-4-[2-(tert-butoxycarbonylamino)phenyl]-L-phenylalanine methyl ester

HRID 24635

Reaktionsgleichung

Reaktionsgleichung von HRID 24635
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20](=[O:41])[C@H:21]([CH2:33][C:34]1[CH:39]=[CH:38][C:37](Br)=[CH:36][CH:35]=1)[NH:22][C:23](=[O:32])[C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:31]>>[CH3:18][O:19][C:20](=[O:41])[C@H:21]([CH2:33][C:34]1[CH:35]=[CH:36][C:37]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:38][CH:39]=1)[NH:22][C:23](=[O:32])[C:24]1[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=1[Cl:30]

Komponenten

3

Edukt 2

HCID 2773226(2-BOC-aminophenyl)boronic acidHCID 54284267N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine methyl ester

Produkt 1

HCID 54237195N-(2,6-dichlorobenzoyl)-4-[2-(tert-butoxycarbonylamino)phenyl]-L-phenylalanine methyl esterAusbeute 73,5 %

Versuchsvorschrift

2-(tert-Butoxycarbonylamino)benzeneboronic acid (0.3 g) was coupled with N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine methyl ester (270 mg) by a similar procedure as described in Examples 15 to give 250 mg of N-(2,6-dichlorobenzoyl)-4-[2-(tert-butoxycarbonylamino)phenyl]-L-phenylalanine methyl ester. ESMS: m/z 543 (MH+).

Quellen und Nachweise

ORD-Eintrag
ord-9e9e7ed7d7784aeeb6a0a3f6851d529b
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855843B2

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