HCID 21667319, compound → HCID 6506250, compound

Participants

Reaction Steps

8.22 g of E-2-formylamino-5-diethylphosphono-3-pentenoic acid ethyl ester are dissolved in 170 ml of 6 N hydrochloric acid and the whole is heated under reflux for 22 hours. After concentration in vacuo, the oily residue is taken up in a small amount of ethanol and the mixture is again concentrated by evaporation in vacuo. This procedure is repeated a further twice. The resulting residue is dissolved in 15 ml of ethanol and 20 ml of ethanol/propylene oxide (1:1) are added dropwise. The resulting brownish-coloured precipitate is filtered off and purified by ion exchange chromatography (Dowex 500W×8/H2O). After concentration and lyophilisation, E-2-amino-5-phosphono-3-pentenoic acid is obtained in the form of a white amorphous powder, 1H-NMR (D2O): 2.39 (dd, 2H, C(5)-H); 4.27 (d, 1H, C(2)-H); 5.53 (m, 1H, C(3)-H); 5.87 (m, 1H, C(4)-H), m.p. after recrystallisation from ethanol/water 191°-192° .

Provenance & Evidence