Glycine → Glyphosate

HRID 342928Notes

Reaction equation

HRID 342928 reaction equation
[C:1]([P:3](=[O:6])([O-:5])[O-:4])#[N:2].[K+].[K+].N[CH2:10][C:11]([OH:13])=[O:12].Cl.O1CCOCC1.[Br-].[Mg+2].[Br-].[H][H]>O.[OH-].[Pd+2].[OH-]>[P:3]([O-:5])([O-:12])([O-:4])=[O:6].[P:3]([CH2:1][NH:2][CH2:10][C:11]([OH:13])=[O:12])([OH:5])([OH:4])=[O:6]

Participants

9

Reactant 5

HCID 750GlycineHCID 82241Magnesium BromideHCID 15367030HCID 15367030, compoundHCID 204431481,4-Dioxane hydrochlorideHCID 178418361HCID 178418361, compound2×

Product 2

HCID 1061PhosphateHCID 3496GlyphosateYield 2.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  1. additioncontaining a magnetic stir bar
  2. filtrationthe reaction mixture was filtered through Celite
  3. washwashed with D2O

Sources & evidence

ORD record
ord-00ba1717d33145f3888ef677767e0d93
Source dataset
uspto-grants-1999_01
Patent number
US05859290

Reaction notes

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