S(=O)(=O)(O)O.N[C:7]1[CH:8]=[C:9]([OH:17])[C:10](=[CH:15][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12].C(Cl)Cl.[C:21]1(=[O:27])[O:26][C:24](=[O:25])[CH2:23][CH2:22]1.Cl.C([N:31](CC)CC)C>>[C:21]([CH2:22][CH2:23][C:24]([NH:31][C:8]1[C:9]([OH:17])=[C:10]([CH:15]=[CH:16][CH:7]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:25])([OH:26])=[O:27]Methyl 4-aminosalicylate bisulfate (5 g) is placed in a 50-mL round bottom flask. The flask is charged with 20 mL of methylene chloride and 15 mL of triethylamine. Finally, succinic anhydride (2.75 g) is added. The reaction mixture is then allowed to stir at ambient conditions overnight. Solvents are removed under reduced pressure, yielding a viscous residue, to which 1 N HCl is added. Methyl (3-carboxy-propionylamino)-2-hydroxybenzoate is yielded as tan powder. The powders are collected by filtration, washed with water, and dried.
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