(Aminomethyl)phosphonic acid → Glyphosate

HRID 363808Notes

Reaction equation

HRID 363808 reaction equation
[NH2:1][CH2:2][P:3](=[O:6])([OH:5])[OH:4].O.[C:8]([OH:12])(=[O:11])[CH:9]=O>[Pd]>[NH2:1][CH2:2][P:3](=[O:4])([OH:6])[OH:5].[CH2:9]([NH:1][CH2:2][P:3]([OH:5])([OH:4])=[O:6])[C:8]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 14017(Aminomethyl)phosphonic acidHCID 15620607Glyoxylic acid, monohydrate

Product 2

HCID 3496GlyphosateHCID 14017(Aminomethyl)phosphonic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Aminomethylphosphonic acid was reductively alkylated with glyoxylic acid hydrate under catalytic hydrogenation conditions in the manner described in Example 2, except that the catalyst used was palladium metal (0.05 g), and the pH of the initial reaction mixture was 4.5. A 27% conversion of aminomethylphosphonic acid was obtained with a 93.7% selectivity to glyphosate.

Workup

  1. customthe pH of the initial reaction mixture

Sources & evidence

ORD record
ord-6b0ffd800a764d7a9a88d4527dff1c5a
Source dataset
uspto-grants-1999_02
Patent number
US05874612

Reaction notes

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