Glyphosate → N-tert-Butylglycine

HRID 1589104Notes

Reaction equation

C(NCP(O)(O)=O)C(O)=O.[C:11]([N:15](CP(O)(O)=O)[CH2:16][C:17]([OH:19])=[O:18])([CH3:14])([CH3:13])[CH3:12].C(N)(C)(C)C>>[C:11]([NH:15][CH2:16][C:17]([OH:19])=[O:18])([CH3:14])([CH3:13])[CH3:12]

Participants

Reactant 3

HCID 3496Glyphosate

HCID 6385Tert-Butylamine

HCID 21917312N-t-butyl-N-phosphonomethylglycine

Product 1

HCID 414246N-tert-Butylglycine

Procedure

Gaertner, U.S. Pat. No. 3,927,080, describes the production of glyphosate by acid hydrolysis of N-t-butyl-N-phosphonomethylglycine or its esters. Tertiary butyl amine is reacted with a bromoacetate ester to produce an ester of N-t-butylglycine which is in turn reacted with formaldehyde and phosphorous acid to produce the N-t-butyl-N-phosphonomethylglycine precursor.

Sources & evidence

ORD record: ord-473546d9bfc0425f8806be533df0559c
Source dataset: uspto-grants-1986_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04568432

Reaction notes

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