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0343997098
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note
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In a typical experimental procedure: Diethyl N-(carboxymethyl)amidinomethylphospnonate (5): 1.0165 g (2.90 mmol) of 4 was added to a stirred mixture of 0.2213 g (2.95 mmol) of glycine, 1.0 mL of dichloromethane and 2.0 mL of pyridine. The mixture was stirred overnight and then filtered to remove solids. After rinsing with dichloromethane, hexanes was added to the filtrate until it was persistently cloudy, and the mixture was placed in a 5 °C refrigerator overnight. The solid was removed by filtration and air dried on the filter after thorough rinsing with cold dichloromethane. The white solid weighs 0.5897 g (44.3%).
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18
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0343560875
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note
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In a typical experimental procedure: N-(Carboxymethyl)amidinomethylphosphonic acid, disodium salt (1): Bromotrimethylsilane (1.5 equiv.) was added to diethyl N-(carboxymethyl)amidinomethyl-phosphonate (1.0 equiv.) and the mixture was stirred at room temperature overnight. The excess TMSBr was evaporated under vacuum. The residue was redissolved in of water and stirred at room temperature for 4 h. The mixture was then lyophilized to dryness. The solid was redissolved in water, loaded onto an anion exchange column (Dowex 1×8-200, HCO3-form) (18 mm × 9.4 cm) and eluted with a linear gradient from 100% water to 1 M TBK (TBK = triethylammonium bicarbonate, prepared by mixing 139 mL of triethylamine in 1 L of water and bubbling CO2 into the mixture until the pH reaches 8.6). The fractions with product were identified by spotting them on a silica plate and staining with ninhydrin. The ones which had material that stained more darkly than triethylamine and ran with TBK were combined and lyophilized to dryness. The solid was lyophilized twice more from 2 mL of water each time to ensure that no TBK remained. The solid was dissolved in water, loaded onto a cation exchange column (Dowex 50×8-100, Na+ form) (10 mm × 9 cm) and eluted with water. Fractions containing product were identified as before, combined and lyophilized to dryness.
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21
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