Glyphosate → N-tert-Butylglycine

Reaction equation

P(CNCC(O)=O)(O)(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 N-phosphonomethylglycine by acid-catalyzed dealkylation of N-t-butyl-N-phosphonomethylglycine or its esters. Tertiary butylamine 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-6c338ea2cef04f129300214f89b16608
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04851131

Reaction notes

Loading…