Reaktionsgleichung
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].S(Cl)([Cl:18])=[O:17].[CH2:20]([N:22](CC)CC)[CH3:21]>>[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([Cl:18])=[O:7])([O-:3])=[O:2].[NH2:22][CH2:20][C:21]([O:8][CH2:6][C:5]1[CH:4]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:17]Komponenten
Versuchsvorschrift
As shown in scheme B, treatment of 2,4-dinitrobenzoic acid with chlorinating agent such as thionyl chloride gave 2,4-dinitrobenzoyl chloride which on further treatment with benzyl glycinate in the presence of triethylamine gave benzyl 2-(2,4-dinitrobenzamido)acetate (intermediate 1). The intermediate 1 is treated either with K18F or K19F in the presence of a catalyst such as kryptofix[2.2.2] or 18-crown-6 to yield benzyl 2-(2-fluoro-4-nitrobenzamido)acetate, which on reduction with hydrogen gas or hydrogen source in the presence of Pd/C gave 2-(4-amino-2-fluorobenzamido)acetic acid (compound 1) in good yield. Alternatively, treatment of 2,4-dinitrobenzoyl chloride with glycine in presence of a mild base such as sodium carbonate gave 2-(2,4-dinitrobenzamido)acetic acid (intermediate 2). Treatment of intermediate 2 either with K18F or K19F gave 2-(2-fluoro-4-nitrobenzamido)acetic acid, which on reduction with zinc dust and ammonium formate or hydrogen gas/hydrogen source in the presence of Pd/C gave compound 1. Treatment of intermediate 2 either with K18F or K19F and further reduction with iron powder in the presence of acetic anhydride-acetic acid gave 2-(4-acetamido-2-fluorobenzamido)acetic acid (compound 2).
Quellen und Nachweise
- ORD-Eintrag
- ord-019a024964ef422eb47b448b4d5e4f65
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08906344B2
Verknüpfte Notizen
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