Triethylamine → Benzyl glycinate
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([OH:9])=[O:8])([O-:3])=[O:2].S(Cl)([Cl:18])=[O:17].[CH2:20]([N:22](CC)CC)[CH3:21]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([Cl:18])=[O:8])([O-:3])=[O:2].[NH2:22][CH2:20][C:21]([O:9][CH2:7][C:6]1[CH:5]=[CH:4][CH:12]=[CH:11][CH:10]=1)=[O:17]Participants
5
Procedure
As shown in scheme C, reaction of 3,4-dinitrobenzoic acid with thionyl chloride gave 3,4-dinitrobenzoyl chloride, which on further treatment with benzyl glycinate in the presence of triethylamine gave benzyl 2-(3,4-dinitrobenzamido)acetate (intermediate 3). The intermediate 3 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-(4-fluoro-3-nitrobenzamido)acetate, which on reduction with hydrogen gas or hydrogen source in the presence of Pd/C gave 2-(3-amino-4-fluorobenzamido)acetic acid (compound 3). In an analogous manner, 2-(5-amino-2-chloro-4-fluorobenzamido)acetic acid (compound 4) is synthesized starting from 2-chloro-4,5-dinitrobenzoic acid.
Sources & evidence
- ORD record
- ord-8819d817728e4ec3b891a66add541967
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906344B2
Reaction notes
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