Potassium Carbonate → N-(2,6-Dichlorobenzoyl)-4-[2-[N-(tert-butyl)sulfamoyl]phenyl]-L-phenylalanine methyl ester

Reaktionsgleichung

[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:24][O:25][C:26](=[O:47])[C@H:27]([CH2:39][C:40]1[CH:45]=[CH:44][C:43](Br)=[CH:42][CH:41]=1)[NH:28][C:29](=[O:38])[C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[Cl:37]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CCOC(C)=O>[CH3:24][O:25][C:26](=[O:47])[C@H:27]([CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6](=[O:8])(=[O:7])[NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:44][CH:45]=1)[NH:28][C:29](=[O:38])[C:30]1[C:31]([Cl:37])=[CH:32][CH:33]=[CH:34][C:35]=1[Cl:36]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

2-[N-(tert-Butyl)sulfamoyl]benzeneboronic acid (0.4 g) was dissolved in DME (10 mL). To this solution was added K2CO3 (0.1 g), N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine methyl ester (0.1 g), Pd(Ph3P)4 (0.1 g) and water (0.2 mL). The mixture was heated at 80° C. overnight. After cooling, EtOAc and water were added to the mixture. The EtOAc phase was dried (MgSO4), filtered and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexanes 1:2) to give 100 mg of the title compound. ESMS: m/z 585 ([M+Na]+).

Aufarbeitung

temperatureAfter cooling
dry with materialThe EtOAc phase was dried (MgSO4)
filtrationfiltered
customevaporated
customThe residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexanes 1:2)

Quellen und Nachweise

ORD-Eintrag: ord-3fbb1750900f439ba20a4652ef70f839
Quelldatensatz: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06855843B2

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