[F:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5](=[CH:7][CH:8]=1)[OH:6].[O:10]=[C:11]1[C:16](=[O:17])[N:15]([CH2:18][CH3:19])[CH2:14][CH2:13][N:12]1[C:20]([NH:22][CH:23](O)[C:24]([OH:26])=[O:25])=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.O>[OH:9][C:4]1[C:5]([OH:6])=[CH:7][C:8]([CH:23]([C:24]([OH:26])=[O:25])[NH:22][C:20]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[C:16](=[O:17])[C:11]2=[O:10])=[O:21])=[C:2]([F:1])[CH:3]=14-Fluorocatechol (3.06 g., 24 mmole) was added to a suspension of N-(2,3-dioxo-4-ethylpiperazin-1-ylcarbonyl)-2-hydroxyglycine (3.89 g, 15 mmole) in glacial acetic acid (13.5 ml) and concentrated sulphuric acid (1.5 ml). The mixture was stirred overnight, diluted with water (50 ml), adjusted to pH6 with saturated sodium carbonate and washed with ethyl acetate (2×50 ml). The aqueous solution was acidified to pH 2.5 and extracted with ethyl acetate (5×40 ml). The combined extracts were dried and evaporated to give the crude product, 6.10 g, as a foam.
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