[CH3:1][N:2]([CH3:30])[C:3]([C:5]1[N:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]3[CH2:27][CH2:26][N:25]([CH3:28])[C:24]3=[O:29])[CH:21]=2)[C:15]([O:17]C)=[O:16])=[N:9][CH:10]=1)=[O:4].CO.[OH-].[Li+].O>C1COCC1>[CH3:1][N:2]([CH3:30])[C:3]([C:5]1[N:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]3[CH2:27][CH2:26][N:25]([CH3:28])[C:24]3=[O:29])[CH:21]=2)[C:15]([OH:17])=[O:16])=[N:9][CH:10]=1)=[O:4]The methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 46) (772 mg, 1.86 mmol) was dissolved in THF (9 mL) and methanol (3 mL) and lithium hydroxide solution (1N, 2.2 mL) was added followed by water (25 mL). The resulting mixture was stirred for 1 hour at room temperature. The majority of the organic solvent was removed by distillation under reduced pressure. The remaining aqueous solution was extracted with ethyl acetate (10 mL) then acidified with 2N citric acid and re-extracted with ethyl acetate (5×25 mL), the combined organic extracts were washed with water (10 mL) and brine (20 mL), dried (MgSO4) and evaporated to afford the product (716 mg, 96%). 1H NMR δ (300 MHz, CDCl3) 2.13-2.27 (m, 1H), 2.55-2.69 (m, 1H), 2.96 (s, 3H), 3.17 (d, 6H), 3.35-3.58 (m, 2H), 4.98 (t, 1H), 7.10 (s, 1H), 7.45 (s, 1H), 7.63 (s, 1H), 8.36 (s, 1H), 8.53 (s, 1H); m/z 401 (M+H+).
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