(Aminomethyl)phosphonic acid → Glyphosate

HRID 1901388Notes

Reaction equation

HRID 1901388 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-083ac860247b4165925586c6eaaa6ffa
Source dataset
uspto-grants-1996_11
Patent number
US05578190

Reaction notes

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