Glycine → Glyphosate

Participants

Reaction Conditions

Reaction Steps

Dipotassium cyanophosphonate (partially hydrated, 0.188 g, 1.03 mmol) was dissolved in water (5 ml) in a Fisher Porter bottle containing a magnetic stir bar, and glycine (0.0828 g, 1.10 mmol) was added. Palladium hydroxide 20% on carbon (0.089 g, Aldrich) was added along with HCl-dioxane, (0.25 ml, 4N, 1 mmol), and magnesium bromide (0.185 g, 1.00 mmol). After three pressure-release cycles with hydrogen, the bottle was pressurized to 25 psi with hydrogen and stirred overnight at 50° C. The pressure was then released, and the reaction mixture was filtered through Celite and washed with D2O. HPLC analysis (system for phosphate analysis) gave a 2.2% yield of N-phosphonomethylglycine.

Provenance & Evidence