C[O:2][C:3](=[O:22])[C:4]1[CH:13]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]([C:8]([O:10]C)=[O:9])=[CH:6][C:5]=1[F:21].O.[OH-].[Li+]>CO.C1COCC1.O>[F:21][C:5]1[CH:6]=[C:7]([C:8]([OH:10])=[O:9])[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][C:4]=1[C:3]([OH:22])=[O:2]A mixture of 174C (30.0 g, 9.89 mmol) and lithium hydroxide monohydrate (12.5 g, 29.7 mmol) in MeOH (200 mL), THF (200 mL) and water (100 mL) was heated at 75° C. for 0.5 h. HPLC indicated that the reaction was complete. The organic solvents were removed under reduced pressure, and the aqueous residue was diluted with water. The pH was adjusted to 3.0 with 6N aqueous hydrochloric acid which resulted in a precipitate. The solid was collected by vacuum filtration and dried under reduced pressure to provide a quantitative yeild of compound 174D as an orange-yellow solid. HPLC retention time=3.02 min. (Condition B). 1H-NMR (400 MHz, DMSO) δ7.11 (m, 1H), 7.25 (m, 2H), 7.39 (m, 2H), 7.60 (m, 1H), 7.68 (m, 1H), 9.32 (br s, 1H), and 13.55 (br s, 2H).
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