Triethylamine → 2-(Benzoyloxy)-3-(octadecyloxy)propyl 3-pyridiniopropyl phosphate

Participants

Reaction Steps

Under ice-cooling, 4.6 g (10 mmole) of 1-octadecyl-2-benzoylglycerol (synthesized according to the procedure of Example 8) in 35 ml of chloroform was added dropwise to a mixture of 70 ml of chloroform, 1.62 g (10.5 mmole) of phosphorus oxychloride and 7.0 ml (52 mmole) of triethylamine over the period of time of 40 minutes. The resulting mixture was stirred at room temperature for 1 hour and then cooled on an ice-bath. 3.9 g (12.6 mmole) of 3-hydroxypropylpyridinium tosylate in 30 ml of pyridine was added dropwise to the mixture and the reaction mixture was stirred at room temperature overnight. An aqueous solution saturated with 7.0 g of sodium hydrogencarbonate was added to the mixture and the resulting mixture was concentrated to dryness under reduced pressure. To the residue were added 100 ml of toluene and 100 ml of dichloromethane and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and then the residue was dissolved in water and subjected to chromatography on columns of 40 ml of Amberlite IRA-410 and 20 ml of Amberlite IR-120 and eluted with water and 95% hydrous tetrahydrofuran. The eluate was concentrated and the residue was subjected to column chromatography of silica gel (50 g) and eluted with chloroform-methanol-water (65:25:4). The desired fractions were concentrated to give 2-(benzoyloxy)-3-(octadecyloxy)propyl 3-pyridiniopropyl phosphate as a colorless solid material. Yield: 2.4 g (yield:37.1%).

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