Glycine → Glyphosate
Reaction equation
[CH:1]([P:3](=[O:6])([OH:5])[OH:4])=O.[NH2:7][CH2:8][C:9]([OH:11])=[O:10].[OH-].[Na+].[H][H]>O.[Pd]>[P:3]([CH2:1][NH:7][CH2:8][C:9]([OH:11])=[O:10])([OH:5])([OH:4])=[O:6]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a 59% aqueous formylphosphonic acid solution (5.0 g, 0.23 mol) in deionized water (25 mL) was added glycine (1.56 g, 0.021 mol). The pH of the resultant mixture was adjusted to 7.0 by addition of 2.5 N sodium hydroxide. The reaction mixture was then transferred to a 300 mL autoclave, a 10% palladium on carbon catalyst (1.0 g) added, and the reactor was sealed and pressurized with hydrogen to 6.89×106 N/m2 gauge. After 60 minutes of reaction at room temperature, 3.2 g of N-(phosphonomethyl)glycine was obtained representing a 91% yield based on glycine.
Workup
- customthe reactor was sealed
- customAfter 60 minutes of reaction at room temperature
Sources & evidence
- ORD record
- ord-3336889f14b54607a222d5ba40490a7e
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06274760B1
Reaction notes
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