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

HRID 1883237Notes

Reaction equation

HRID 1883237 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-c2058d40a6f2492881f7155f18741e8c
Source dataset
uspto-grants-2004_07
Patent number
US06759549B2

Reaction notes

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