Glycine → Glyphosate

HRID 342927Notes

Reaction equation

HRID 342927 reaction equation
[C:1]([P:3](=[O:6])([O-:5])[O-:4])#[N:2].[Na+].[Na+].N[CH2:10][C:11]([OH:13])=[O:12].Cl.O1CCOCC1.[H][H]>O.[Pd]>[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

8

Reactant 4

HCID 750GlycineHCID 15367023HCID 15367023, compoundHCID 204431481,4-Dioxane hydrochlorideHCID 178418361HCID 178418361, compound2×

Product 2

HCID 1061PhosphateHCID 3496GlyphosateYield 1.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Disodium cyanophosphonate (partially hydrated) (0.170 g, 1.06 mmol) was dissolved in water (5 ml) in a Fisher Porter bottle containing a magnetic stir bar, and glycine (0.0862 g, 1.148 mmol) was added. Three percent palladium on carbon (0.060 g, prepared as per Example 3) was added along with HCl-dioxane (0.25 ml, 4N, 1 mmol). After three pressure-release cycles with hydrogen, the bottle was pressurized to 25 psi with hydrogen and stirred overnight at ambient temperature. The pressure was released, and the reaction mixture was filtered through Celite and washed with D2O. HPLC analysis (system for phosphate analysis) gave a 1.2% 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-f65640c2054c4820902530f431cd936a
Source dataset
uspto-grants-1999_01
Patent number
US05859290

Reaction notes

Loading…