Reaktionsgleichung
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[NH2:16][C@H:17]([C:19]([OH:21])=[O:20])[CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>>[N+:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[C:6]([NH:16][C@@H:17]([CH3:18])[C:19]([OH:21])=[O:20])=[O:8])([O-:15])=[O:14]Komponenten
Versuchsvorschrift
As shown in scheme 1,2,6-dinitrobenzoyl chloride prepared from 2,6-dinitrobenzoic acid is treated with L-alanine in the presence of sodium carbonate to yield (S)-2-(2,6-dinitrobenzamido)propanoic acid (intermediate 13). Treatment of intermediate 13 either with K18F or K19F gave (S)-2-(2-fluoro-6-nitrobenzamido)propanoic acid, which on reduction with iron powder in the presence of acetic acid gave (S)-2-(2-amino-6-fluorobenzamido)propanoic acid (compound 12). In an analogous manner, treatment of 2,6-dinitrobenzoyl chloride with D-alanine gave (R)-2-(2,6-dinitrobenzamido)propanoic acid (intermediate 14), which on treatment either with K18F or K19F and further reduction with iron powder gave (R)-2-(2-amino-6-fluorobenzamido)propanoic acid (compound 13).
Quellen und Nachweise
- ORD-Eintrag
- ord-c2928b2fe52648f1bdffece2afa0d3cc
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08906344B2
Verknüpfte Notizen
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