Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetate → Methyl 2-amino-2-(dimethoxyphosphoryl)acetate

HRID 1058404Notes

Reaction equation

HRID 1058404 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

HCID 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetate

Product 1

HCID 11084793Methyl 2-amino-2-(dimethoxyphosphoryl)acetateYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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.

Workup

  1. filtrationThe solution was filtered through Celite®
  2. concentrationthe filtrate was concentrated
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-3c2c87b865a9422db89bb82bb6fa5e2a
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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