Trimethyl phosphite → Methyl ((tert-butoxy(hydroxy)methylidene)amino)(dimethoxyphosphoryl)acetate

Participants

Reaction Conditions

Reaction Steps

A quantity of 2.92 g (0.016 mol) of N-bromo succinimide is added to 2.82 g (0.015 mol) of N-Boc glycine, methyl ester in 230 mL of carbon tetrachloride. The mixture is heated at reflux with stirring for 1 hour, cooled to 0° C., and filtered. The filtrate is evaporated to dryness and the residue is dissolved in 30 mL of tetrahydrofuran. A quantity of 2.10 g (0.017 mol) of trimethyl phosphite is added and the solution is maintained at reflux for 18 hours. The solvent is evaporated and the product is purified by silica gel chromatography eluting with ethyl acetate; wt 2.80 g (63%);

Provenance & Evidence