Phosphonic acid → N-methyl-N-(phosphonomethyl)glycine

HRID 1883240Notes

Reaction equation

HRID 1883240 reaction equation
[C:1]([N:4]([CH2:6][C:7]([OH:9])=[O:8])[CH3:5])(=O)C.C=O.[OH:12][PH:13]([OH:15])=[O:14].P(Cl)(Cl)Cl>>[P:13]([CH2:1][N:4]([CH3:5])[CH2:6][C:7]([OH:9])=[O:8])([OH:15])([OH:14])=[O:12]

Participants

5

Reactant 4

HCID 407Phosphonic acid2×HCID 712FormaldehydeHCID 24387Phosphorus trichlorideHCID 10975514N-Acetyl-N-methylglycine

Product 1

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

Procedure

As depicted, the carboxymethylation step of Reaction Scheme 12 is the same as the carboxymethylation step of Reaction Schemes 10 and 11. In Reaction Scheme 12, however, N-acetylsarcosine XX is reacted with formaldehyde and H3PO3, PCl3 or other H3PO3 source to produce N-(phosphonomethyl)-N-methyl-glycine XXI which is oxidized in the presence of a platinum catalyst and oxygen to Glyphosate I and acetic acid. The acetic acid is then reacted with methylamine to yield the N-methylacetamide starting material.

Workup

  1. customthe carboxymethylation step of Reaction Scheme 12
  2. customsame as the carboxymethylation step of Reaction Schemes 10 and 11
  3. customIn Reaction Scheme 12

Sources & evidence

ORD record
ord-8c832eb7bc8d4f5187a1d8659c503e99
Source dataset
uspto-grants-2004_07
Patent number
US06759549B2

Reaction notes

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