Benzyl Alcohol → dibenzyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate

Participants

Reaction Steps

To a suspension of 3.0 g (9.3 mmol) of diethyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate in 19.1 ml (185.6 mmol) of benzyl alcohol are added 40 ml of a 4N solution of hydrochloric acid in diethyl ether. The solution formed is allowed to stand for 1 week. The reaction mixture is evaporated to dryness. The residue is dissolved in 35 ml of ethanol, and a solution of 35 ml of propylene oxide in 35 ml of ethanol is added. The crystalline precipitate formed is collected, re-crystallized twice from water and dried over phosphorus pentoxide, affording dibenzyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate of m.p. 220°-221° (decomp).

Provenance & Evidence