C1O[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=3[C:21]#[N:22])[CH2:7][CH2:6]2)[O:4]C1C.Cl.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>CCOCC>[C:21]([C:12]1[CH:13]=[C:14]([C:17]([F:19])([F:20])[F:18])[CH:15]=[CH:16][C:11]=1[N:8]1[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]1)#[N:22]A solution of 24 (1.70 g, 5.20 mmol) in ether (20 mL) was treated with 6N aqueous HCl (50 mL). The mixture was stirred at room temperature (20 min). The reaction mixture was neutralized with sodium carbonate solution and solid sodium hydroxide. The aqueous layer was extracted with two additional portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 6 mm, 10% EtOH-90% CHCl3) afforded the title compound (25).
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