[H-].[K+].[CH2:3]([O:5][P:6]([CH2:11][S:12]([O:15][CH2:16][CH3:17])(=[O:14])=[O:13])([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].Cl[CH2:19][C:20]1[C:25]([CH2:26]Cl)=[CH:24][CH:23]=[CH:22][N:21]=1>CS(C)=O>[CH2:3]([O:5][P:6]([O:8][CH2:9][CH3:10])([C:11]1([S:12]([O:15][CH2:16][CH3:17])(=[O:13])=[O:14])[CH:19]=[C:20]2[C:25]([CH:24]=[CH:23][CH2:22][NH:21]2)=[CH:26]1)=[O:7])[CH3:4]To an ice bath chilled solution of 35% potassium hydride in mineral oil (5.0 mmol) stirring under argon DMSO (7 ml) is added a solution of diethoxyphosphinyl methanesulfonic acid, ethyl ester (2.5 mmol) [prepared as described in J. C. Carretero, et. al., Tetrahedron, Vol. 43, pp. 5125-5134 (No. 21) 1987] in DMSO (5 ml). On completion of a dropwise addition, the resulting solution is stirred at room temperature for one hour. A solution of 2,3-bis(chloromethyl)pyridine (2.5 mmol) [prepared as described in K. Tsuda, et. al., Chem. Pharm. Bull., Vol.1, pp. 142, 1953] in DMSO (2 ml) is added slowly and the reaction mixture is then heated at 90° C. for 1 hour. After cooling, the reaction mixture is concentrated under reduced pressure and the desired product is purified by flash chromatography using a 5-15% isopropanol in methylene chloride gradient on silica gel.
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