Phosphonic acid → 2-[N-(phosphonomethyl)acetamido]acetic acid

HRID 1386849Notes

Reaction equation

HRID 1386849 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[CH2:9]=O.[OH:11][PH:12]([OH:14])=[O:13].P(Cl)(Cl)Cl>>[P:12]([CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][C:6]([OH:8])=[O:7])([OH:14])([OH:11])=[O:13]

Participants

5

Reactant 4

HCID 407Phosphonic acid2×HCID 712FormaldehydeHCID 10972AcetylglycineHCID 24387Phosphorus trichloride

Product 1

HCID 235108502-[N-(phosphonomethyl)acetamido]acetic acid

Procedure

In contrast to Reaction Scheme 6, however, N-acetylglycine XVIII is reacted with formaldehyde and H3PO3, PCl3 or other H3PO3 source to produce N-(phosphonomethyl)-N-acetylglycine XIX which is hydrolyzed using water and an acid such as hydrochloric acid to produce Glyphosate 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.

Workup

  1. customIn contrast to Reaction Scheme 6

Sources & evidence

ORD record
ord-1dc0f74613374e3287e619c514266c22
Source dataset
uspto-grants-2001_07
Patent number
US06265605B1

Reaction notes

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