Sodium Iodide → Benzyl glycinate

Participants

Reaction Steps

A mixture of 0.36 g (0.67 mmol) of 3-(octadecyloxy)-5-[(tricyclo[3.3.1.1/3,7/]dec-1-ylcarbonyl)oxy]benzenamine, 0.31 mL (2.0 mmol) of benzylbromoacetate, 0.44 g (2.0 mmol) of 1,8-bis(dimethylamino)naphthalene and 0.11 g (0.7 mmol) of sodium iodide in 10 mL of acetonitrile and 13 mL of DMF was stirred and refluxed under argon for 72 hours. The solvents were removed at reduced pressure, ethyl acetate was added to the residue and the extract was washed with 0.01 N HCl, with NaHCO3 solution, dried and concentrated at reduced pressure to an oil. Purification by chromatography on 75 g of silica gel using 15% ethyl acetate-hexane gave 0.177 g of N-[[3-(octadecyloxy)-5-(tricyclo[3.3.1.1/3,7/]dec-1-ylcarbonyl)oxy]phenyl]glycine phenylmethyl ester as an oil. The nmr and mass spectra were consistent with the structure. A mixture of 0.17 g of N-[[3-(octadecyloxy)-5-tricyclo[3.3.1.1/3,7/]dec-1-ylcarbonyl)oxy]phenyl]glycine phenylmethyl ester and 0.1 g of 10% palladium on carbon was shaken under an initial hydrogen pressure of 54 psi on a Parr Hydrogenator for 2.5 hours. The catalyst was removed at reduced pressure and the filtrate was concentrated at reduced pressure to 0.12 g of N-[[3-(octadecyloxy)-5-(tricyclo[3.3.1.1/3,7/]dec-1-ylcarbonyl)oxy]phenyl]glycine as a semisolid. The nmr and mass spectra were consistent with the structure.

Provenance & Evidence