[CH2:1]1COCC1.[O:6]=[C:7]1[C@@H:13]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:12][CH2:11][C:10]2[CH:22]=[CH:23][CH:24]=[CH:25][C:9]=2[NH:8]1.CI>[H-].[Na+].CCOC(C)=O.CCCCCCC.CCOC(C)=O>[CH3:1][N:8]1[C:9]2[CH:25]=[CH:24][CH:23]=[CH:22][C:10]=2[CH2:11][CH2:12][C@H:13]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[C:7]1=[O:6]
0.898 mg of sodium hydride in suspension at 60% in oil (22.44 mmol) is introduced, at AT, into a 500 ml round-bottomed flask, with stirring and under an argon atmosphere, containing 260 ml of THF and 6.2 g of 2a (22.44 mmol). The medium is stirred for 1 h and then 3.823 g (26.94 mmol) of methyl iodide are added. The medium is left stirring overnight, 500 ml of EtOAc are added and the organic phase is washed twice with 500 ml of water. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. 6.85 g of crude product are obtained. After chromatography on a silica cartridge (250 g, eluent heptane/EtOAc—as an EtOAc gradient: 10 to 50%). 4.47 g of product 7a (white solid) are obtained.
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