Glycine ethyl ester → Glyphosate

HRID 342929Notes

Reaction equation

HRID 342929 reaction equation
[C:1]([P:3](=[O:6])([O-:5])[O-:4])#[N:2].[Li+].[Na+].C([O:11][C:12](=[O:15])[CH2:13]N)C.[H][H]>O.[Pd]>[P:3]([O-:5])([O-:11])([O-:4])=[O:6].[P:3]([CH2:1][NH:2][CH2:13][C:12]([OH:15])=[O:11])([OH:5])([OH:4])=[O:6]

Participants

7

Reactant 3

HCID 12176Glycine ethyl esterHCID 86753577HCID 86753577, compoundHCID 178418361HCID 178418361, compound2×

Product 2

HCID 1061PhosphateHCID 3496GlyphosateYield 0.93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Sodium lithium cyanophosphonate was dissolved in water in a Fisher Porter bottle containing a magnetic stir bar, and glycine ethyl ester was added. A catalyst of 5% palladium on carbon (Lot #323810, water 52.38%, Engelhard) was added. 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 0.93% 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-402a5e8b80e14936b92ba79b3280ce19
Source dataset
uspto-grants-1999_01
Patent number
US05859290

Reaction notes

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