[H-].[Na+].[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7](=[O:15])[C@@H:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:5]1.[CH3:24]I>C1COCC1>[CH3:24][N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:4]([CH3:3])[CH2:5][C@H:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[C:7]1=[O:15]36 mg of sodium hydride in suspension at 60% in oil (0.90 mmol) are introduced at −10° C. into a 50 mL round-bottomed flask, with stirring and under an argon atmosphere, containing 10 mL of THF and 265 mg of 11 (0.91 mmol). The medium is stirred for 1 h, and then 148 mg (1.04 mmol) of methyl iodide are added. The medium is kept stirring at RT for 24 h. The mixture is concentrated, and 320 mg of crude product are obtained, which product is chromatographed on a silica cartridge (50 g, eluent heptane/AcOEt—in an AcOEt gradient: 10 to 50%). 235 mg of expected product 17 are recovered.
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