Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12](=[O:15])[CH2:13]Cl)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH:16]([NH2:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[I-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12](=[O:15])[CH2:13][NH:29][CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]Participants
6
Procedure
1.0 g (4.0 mmol) of 5-chloro-2-[(chloroacetyl)amino]benzoic acid obtained in Example 72-(i), 2.94 g (16.0 mmol) of benzhydrylamine, and 60 mg (0.4 mmol) of sodium iodide were stirred in 3 mL of DMF solution at 80° C. for 1 hour. Thereafter, the mixture was diluted with ethyl acetate, and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. Ethyl acetate was added to the condensed residue, and solids were collected by filtration, followed by drying, thereby giving 744 mg of the target 5-chloro-2-{[N-(diphenylmethyl)glycyl]amino}benzoic acid (yield: 49%).
Workup
- washwashed with 1N hydrochloric acid
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- additionEthyl acetate was added to the condensed residue, and solids
- filtrationwere collected by filtration
- customby drying
Sources & evidence
- ORD record
- ord-3d7be04a68e4440b9598f4d2a2b67d72
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785473B2
Linked notes
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