Phosphonic acid → Glyphosate

HRID 1883238Notes

Reaction equation

HRID 1883238 reaction equation
O=[C:2]1CN[C:5](=[O:8])[CH2:4][NH:3]1.C=[O:10].[OH:11][PH:12]([OH:14])=[O:13].P(Cl)(Cl)Cl>C(O)(=O)C>[P:12]([CH2:2][NH:3][CH2:4][C:5]([OH:8])=[O:10])([OH:14])([OH:11])=[O:13]

Participants

6

Reactant 4

HCID 407Phosphonic acid2×HCID 712FormaldehydeHCID 78172,5-PiperazinedioneHCID 24387Phosphorus trichloride

Product 1

HCID 3496Glyphosate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The sequence of reactions in Reaction Scheme 9a is comparable to those set forth in Reaction Scheme 9 except that N-acetylglycine XVIII is deacylated to form 2,5-diketopiperazine XXX. 2,5-diketopiperazine XXX is then reacted with formaldehyde and H3PO3, PCl3 or other H3PO3 source to produce N-(phosphonomethyl)glycine I and acetic acid. Acetic acid which is produced in the hydrolysis step can be reacted with ammonia to generate acetamide for the carboxymethylation step.

Sources & evidence

ORD record
ord-7544217d5e4645538d074d85bacd8019
Source dataset
uspto-grants-2004_07
Patent number
US06759549B2

Reaction notes

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