Acetamide → 2,2'-(2,5-Dioxopiperazine-1,4-diyl)diacetic acid

HRID 1859237Notes

Reaction equation

HRID 1859237 reaction equation
[CH2:1]([NH:5][CH2:6]P(O)(O)=O)[C:2]([OH:4])=[O:3].C(N)(=O)C.[C:15]([N:18]([CH2:23][C:24](O)=[O:25])[CH2:19][C:20]([OH:22])=[O:21])(=[O:17])C>>[C:2]([CH2:1][N:5]1[CH2:6][C:15](=[O:17])[N:18]([CH2:19][C:20]([OH:22])=[O:21])[CH2:23][C:24]1=[O:25])([OH:4])=[O:3]

Participants

4

Reactant 3

HCID 178AcetamideHCID 3496GlyphosateHCID 10130190N-acetyliminodiacetic acid

Product 1

HCID 235108522,2'-(2,5-Dioxopiperazine-1,4-diyl)diacetic acid

Procedure

An alternative route for the preparation of glyphosate I from acetamide VII is illustrated in Reaction Scheme 7 ##STR15## In general, the sequence of reactions in Reaction Scheme 7 is the same as those in Reaction Scheme 6 except that N-acetyliminodiacetic acid XVI is deacylated to form 1,4-di(carboxymethyl)-2,5-diketopiperazine XVII which is then directly phosphonomethylated in the same manner as iminodiacetic acid XIV is phosphonomethylated in Reaction Scheme 6.

Workup

  1. customis illustrated in Reaction Scheme 7 ##STR15## In general
  2. customthe sequence of reactions in Reaction Scheme 7

Sources & evidence

ORD record
ord-6b4ef70a4d264e83a152f377b0b70d0b
Source dataset
uspto-grants-2000_11
Patent number
US06153753

Reaction notes

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