Glyphosate → N-acetyliminodiacetic acid

HRID 1859242Notes

Reaction equation

P(CN[CH2:7][C:8]([OH:10])=[O:9])(O)(O)=O.[C:11]([NH:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:13])[CH3:12]>>[C:11]([N:14]([CH2:7][C:8]([OH:10])=[O:9])[CH2:15][C:16]([OH:18])=[O:17])(=[O:13])[CH3:12]

Participants

Reactant 2

HCID 3496Glyphosate

HCID 10972Acetylglycine2×

Product 1

HCID 10130190N-acetyliminodiacetic acid

Procedure

The preparation of N-(phosphonomethyl)glycine starting from N-acetglycine XVIII is depicted in Reaction Schemes 13 and 14. In this Reaction Scheme, N-acetglycine XVIII is carboxymethylated to yield N-acetyliminodiacetic acid XVI which is then converted to Glyphosate I as described in Reaction Schemes 6, 7, and 8.

Workup

customis depicted in Reaction Schemes 13 and 14

Sources & evidence

ORD record: ord-d99194c3553c4c938062051baf364605
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153753

Reaction notes

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