S(Cl)(Cl)=[O:2].[C:5]1([CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:12]([NH2:16])[CH:13]([CH3:15])[CH3:14].C(N(CC)CC)C.[CH3:24][CH2:25][CH2:26]CCCC>CN(C)C=O>[CH3:24]/[CH:25]=[CH:26]/[CH:6]=[CH:7]\[CH2:8][CH2:9]/[CH:10]=[CH:5]/[C:11]([NH:16][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:2]30.2 g (180.5 mmol) of the triene carboxylic acid obtained in the above-mentioned Example B2(1) was dissolved in 90 ml of heptane and 12 ml of dimethylformamide (DMF), and 14.5 ml (1.1 eq) of thionyl chloride was added dropwise thereto by spending 1 hour, while stirring under ice-cooling. After completion of the dropwise addition and subsequent 1 hour of stirring, separation of liquid was carried out by adding 60 ml of water. A heptane solution of the thus obtained acid chloride was added dropwise to a mixture of 60 ml of toluene, 21.5 ml (1.2 eq) of isobutylamine and 30.2 ml (1.2 eq) of triethylamine, by spending 2 hours under ice-cooling, and after completion of the dropwise addition, stirring was carried out at room temperature for 2 hours. The organic layer was separated by adding 120 ml of water, and the organic layer was washed with 120 ml of 0.1 N NaOH aqueous solution and then washed twice with 120 ml of water. By subjecting the thus obtained organic layer to solvent evaporation under a reduced pressure, 35.3 g of the target spilanthol (yield 88%)
불러오는 중…
