Triethylamine → 2-(Benzyloxy)-3-(octadecyloxy)propyl 8-trimethylammoniooctyl phosphate

Participants

Reaction Conditions

Reaction Steps

2.61 g (6.0 mmole) of 2-benzyloxy-3-octadecyloxypropanol was dissolved in 20 ml of chloroform freed of ethanol, and 3.03 g (30.0 mmole, 5.0 eq) of dry triethylamine was added to the mixture with stirring under ice-cooling. Then, 970 mg (6.3 mmole, 1.05 eq) of phosphorus oxychloride dissolved in 40 ml of chloroform freed of ethanol was added to the mixture. The resulting mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. Then, the mixture was cooled to 0° C. and 2.80 g (7.8 mmole, 1.3 eq) of 8-trimethylammoniooctanol monotosylate suspended in 60 ml of dry pyridine was dropwise added thereto over a period of 20 minutes. The mixture was stirred at 0° C. for 1 hour and at room temperature for 3 days. 50 ml of an aqueous solution saturated with sodium hydrogencarbonate was added the reaction mixture, which was concentrated to dryness under reduced pressure. The residue was purified by column chromatography on Amberlite resin (30 ml of IR-120, 15 ml of IR-410; eluent: 95% tetrahydrofuran).

Provenance & Evidence