Sodium Iodide → Benzyl glycinate

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 0.01N HCl, with NaHCO3 solution, dried and concentrated at reduced pressureto 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.

1. temperaturerefluxed under argon for 72 hours
2. customThe solvents were removed at reduced pressure, ethyl acetate
3. additionwas added to the residue
4. washthe extract was washed with 0.01N HCl, with NaHCO3 solution
5. customdried
6. concentrationconcentrated at reduced pressureto an oil
7. customPurification by chromatography on 75 g of silica gel using 15% ethyl acetate-hexane

ORD record

ord-47dc945b7e16429bbea479a6be53537a

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05446189