prop-2-enyl 2-aminoacetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.02 mol glycine allyl ester in 40 mL of THF is added dropwise to a solution of 0.02 mol of 4-isocyanatoacetophenone and 5 mL of pyridine in 40 mL of THF and the reaction mixture is stirred for 3 hours. The solvent is then removed by rotary evaporator. The residue is dispersed in 50 mL of CH3OH, and 0.022 mol of hydroxylamine hydrochloride and 0.06 mol of trimethyl orthoformate are added. The reaction mixture is heated to reflux for 1 hour. The solvent is removed by rotary evaporator to give the product, N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyloxycarbonylmethylurea. The solvent is then removed by rotary evaporator The residue is dispersed in 50 mL of CH3OH The reaction mixture is heated to reflux for 1 hour The solvent is removed by rotary evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.35 mol diphosgene is added dropwise over 1 hour to a mixture of 0.28 mol of glycine allyl ester, prepared as described by H. Waldmann and H. Kunz in Liebigs Ann. Chem., 1983, 1712-1725, and 0.4 g activated charcoal in 400 mL dioxane under N2. The reaction mixture is then heated and stirred at reflux for 21/2 hours. The reaction mixture is then cooled, filtered, and concentrated to dryness by rotary evaporator, keeping exposure to moisture to a minimum. The crude product is re-dissolved in 100 mL THF, and the pH of the solution is adjusted to 5.5-6.0 by addition of pyridine. The product mixture is again filtered, and the product is purified by fractional distillation to give glycine allyl ester isocyanate. prepared The reaction mixture is then heated at reflux for 21/2 hours The reaction mixture is then cooled filtered concentrated to dryness by rotary evaporator The crude product is re-dissolved in 100 mL THF the pH of the solution is adjusted to 5.5-6.0 by addition of pyridine The product mixture is again filtered the product is purified by fractional distillation