Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetate → Methyl 2-amino-2-(dimethoxyphosphoryl)acetate
Reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([P:16]([O:20][CH3:21])([O:18][CH3:19])=[O:17])[NH:5]C(OCC1C=CC=CC=1)=O>[Pd].CO>[CH3:1][O:2][C:3](=[O:22])[CH:4]([P:16]([O:18][CH3:19])([O:20][CH3:21])=[O:17])[NH2:5]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of rac.-N-(benzyloxycarbonyl)-2-(dimethoxyphosphinyl)glycine methyl ester (3.5 g, 10.56 mmol) and 10% palladium on carbon (0.5 g) in methanol (75 mL) was hydrogenated at 50 psi for 1 h. The solution was filtered through Celite® and the filtrate was concentrated and then dried under high vacuum to furnish rac.-2-(dimethoxy-phosphinyl)glycine methyl ester as an clear oil (2.0 g, 96% yield). The amine prepared in this manner was used per se in subsequent reactions.