[CH2:1]([NH:8][C:9]([C:28]1([C:31](O)=[O:32])[CH2:30][CH2:29]1)([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:16][CH:15]=1)[C:10]([F:13])([F:12])[F:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[CH2:1]([N:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][C:24]([F:26])([F:27])[F:25])=[CH:16][CH:15]=2)([C:10]([F:12])([F:11])[F:13])[C:28]2([CH2:30][CH2:29]2)[C:31]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1To a solution of Intermediate 14E (506 mg, 1.1 mmol) in CH2Cl2 (11 mL) was added oxalyl chloride (0.12 mL, 2.2 mmol) followed by several drops of DMF. The reaction was stirred at rt for 16 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (24 g silica gel, eluted with EtOAc in hexanes) to provide Intermediate 14F (389 mg, 72%) as a yellow oil. LCMS Anal. Calc'd for C23H21F6NO2 457.41, found [M+H] 458.2.
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