Glyphosate → N-tert-Butylglycine

HRID 1906983Notes

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-2b7043972e844c9fa0812153b2358683
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04654429

Reaction notes

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