Glyphosate → N-methyl-N-(phosphonomethyl)glycine

HRID 2290659Notes

Reaction equation

[P:1]([CH2:5][NH:6][CH2:7][C:8]([OH:10])=[O:9])([OH:4])([OH:3])=[O:2].P([CH2:15]N[C@H](C(O)=O)C)(O)(O)=O>>[CH3:15][N:6]([CH2:5][P:1]([OH:4])([OH:3])=[O:2])[CH2:7][C:8]([OH:10])=[O:9]

Participants

Reactant 2

HCID 3496Glyphosate2×

HCID 54256951HCID 54256951, compound

Product 1

HCID 541499N-methyl-N-(phosphonomethyl)glycine

Procedure

Liquid chromatography analysis of the recrystallized product showed that N-phosphonomethylglycine was present along with a sister compound whose peak on the chromatogram was of an intensity equal to that exhibited by glyphosate. The sister compound was understood to be N-phosphonomethylalanine. No N-methylglyphosate was formed, but a measurable trace of N-formylglyphosate was observed.

Sources & evidence

ORD record: ord-8b5ca2ef4b1b42018d745dcae1fb236f
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04617415

Reaction notes

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