[CH2:1]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[P:2](=[O:9])([O:6][CH2:7][CH3:8])[O:3][CH2:4][CH3:5].[H-].[Na+].[H-].[CH2:21]([NH:25][C:26](=[O:29])[CH2:27]Cl)[CH2:22][CH2:23][CH3:24].[I-].[K+].[Cl-].[Na+]>C1COCC1>[CH2:21]([NH:25][C:26](=[O:29])[CH2:27][CH:1]([P:2]([O:6][CH2:7][CH3:8])([O:3][CH2:4][CH3:5])=[O:9])[P:10]([O:11][CH2:12][CH3:13])([O:14][CH2:15][CH3:16])=[O:17])[CH2:22][CH2:23][CH3:24]Tetraethyl methylenebisphosphonate (1.44 g, 5.0 mmol) in THF (1 mL) was added to a slurry of 80% sodium hydride (150 mg, 5.0 mmol) in THF (4 mL) at 0° C. The reaction was warmed to room temperature and stirred until all of the hydride was consumed. A solution of N-butyl-2-chloroacetamide (0.75 g, 5.0 mmol) in THF (1 ml) and potassium iodide (100 mg) were then added. The reaction mixture was then heated at 50° C. for 18 hours, during which time sodium chloride precipitated. Additional sodium hydride (20 mg) was added, and the reaction mixture was heated an additional 4 hours. After cooling, the mixture was poured into 1N HCl (10 mL) and diethyl ether (50 mL) was added. The diethyl ether layer was further extracted with water (3×10 mL). The combined aqueous fractions were extracted with dichloromethane (4×25 mL). The combined extracts were dried (Na2SO4) and concentrated to give the title compound (1.40 g, 70%) as an oil.
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