Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[N+:22]([O-])([OH:24])=[O:23]>C1COCC1>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of N-(tert-butoxycarbonyl)-L-tyrosine methyl ester (5.64 g) in THF (10 ml) was added NH4NO3 (3 g) and concentrated HNO3 (3 ml). After 30 sec., the reaction mixture turned to dark red with reflux occurring. The reaction mixture was quenched with solid NaHCO3 and H2O, and extracted with AcOEt. The extract was dried over Na2SO4 and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluent; Hexane→1:1, Hexane/AcOEt) to give N-(tert-butoxycarbonyl)-3-nitro-L-tyrosine methyl ester (3.42 g). The obtained compound was treated in a similar manner as described in R. Example 4 to give 3-Nitro-L-tyrosine methyl ester, hydrochloride salt.
Aufarbeitung
- temperaturewith reflux
- customThe reaction mixture was quenched with solid NaHCO3 and H2O
- extractionextracted with AcOEt
- dry with materialThe extract was dried over Na2SO4
- customthe solvent was removed in vacuo
- customThe residue was purified by column chromatography on silica gel (eluent; Hexane→1:1, Hexane/AcOEt)
Quellen und Nachweise
- ORD-Eintrag
- ord-50bfa75144c34bf7995b8cf121ecb483
- Quelldatensatz
- uspto-grants-2003_07
- Patentnummer
- US06596752B1
Verknüpfte Notizen
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