Sodium Iodide → HCID 19388980, compound

Participants

Reaction Steps

A mixture of 1.82 g (3.27 mmol) of [3-[3-amino-5-(octadecyloxy)phenoxy]propyl]phosphonic acid diethyl ester, 1.6 ml (9.82 mmol) of benzyl bromoacetate, 1.8 g (8.19 mmol) of 1,8-bis-(dimethylamino)naphthalene and 0.14 g (0.92 mmol) of sodium iodide in 40 ml of acetronitrile and 15 ml of DMF was stirred at reflux under argon for 48 hours. The reaction mixture was concentrated at reduced pressure and the residue was dissolved in ethyl acetate. The extract was washed with 0.05N HCl, dried and concentrated a reduced pressure to an oil which was purified by HPLC using 55% ethyl acetate-hexane. This gave 2.41 g (86% yield) of N-[3-[3-(diethoxyphosphinyl)propoxy-5-(octadecyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester as an oil. The structure was confirmed by nmr and mass spectra.

Provenance & Evidence