[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=C2C(O)=O)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:22].C[CH2:24][O:25][C:26]([CH3:28])=[O:27]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:22])[C:10]([CH3:15])=[C:28]2[C:26]([O:25][CH3:24])=[O:27])=[CH:6][CH:7]=1The product from Example 4, Step 2 (1.0 g, 3.6 mmol, 1.0 equiv) was dissolved in DMF (36 mL) and cooled to 0° C. Sodium Hydride (144 mg, 60% in mineral oil, 3.6 mmol, 1.0 equiv) was added, followed by iodomethane (222 μL, 3.6 mmol, 1.0 equiv). The reaction was allowed to warm to room temperature and stirred for 2 hours. Additional portions of NaH (72 mg, 1.8 mmol, 0.50 equiv) and iodomethane (111 μL, 1.8 mmol, 0.50 equiv) were added and the reaction was stirred for one hour. The reaction mixture was diluted with water and EtOAc. The phases were separated and the organic phase was washed twice with satd. NaCl, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (linear gradient 10→50% EtOAc/Hexanes) to afford 470 mg of the title compound (45%) as an off-white powder. MS (ES+) m/e 294 [M+H]+.
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