Tetradecyl phosphocholine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Various phosphocholine derivatives were synthesized using a three-step process as shown in FIGS. 1-2. Specifically, 0.484 grams of hexadecanol (n=15) (from Aldrich Chemical Company) was mixed with 20 milliliters of toluene and 100 milliliters of phosphoryl chloride (“POCl3”). The mixture was heated in an oil bath at 87 to 90° C. for 5 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuum. 50 milliliters of methylene chloride and 1.38 grams of choline tosylate were then stirred into the mixture at room temperature for 40 to 50 hours. This reaction mixture was concentrated by a rotavaporator and the resulting residue was mixed with 1.5 milliliters of water. The residue was stirred at room temperature for 5 hours and concentrated with a nitrogen stream to give crude hexadecyl phosphocholine. Tetradecyl phosphocholine (C14 chain) and docosanoyl phosphocholine (C22 chain) were also synthesized using the technique described above, except that tetradecanol (n=13) and docosanoyl alcohol (n=21) were used to as starting materials instead of hexadecanol. Further, as shown in FIG. 2, the procedure set forth above was also used to synthesize hexadecyl thiophosphocholine, except that thiophosphoryl chloride was used instead of phosphoryl chloride. The expected molecular ion and the corresponding mass spectral results for each synthesized phosphocholine or thiophosphocholine derivatives were determined using mass spectral analysis. The results are shown below in Table 1.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Various phosphocholine derivatives were synthesized using a three-step process as shown in FIGS. 1-2. Specifically, 0.484 grams of hexadecanol (n=15) (from Aldrich Chemical Company) was mixed with 20 milliliters of toluene and 100 milliliters of phosphoryl chloride (“POCl3”). The mixture was heated in an oil bath at 87 to 90° C. for 5 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuum. 50 milliliters of methylene chloride and 1.38 grams of choline tosylate were then stirred into the mixture at room temperature for 40 to 50 hours. This reaction mixture was concentrated by a rotavaporator and the resulting residue was mixed with 1.5 milliliters of water. The residue was stirred at room temperature for 5 hours and concentrated with a nitrogen stream to give crude hexadecyl phosphocholine. Tetradecyl phosphocholine (C14 chain) and docosanoyl phosphocholine (C22 chain) were also synthesized using the technique described above, except that tetradecanol (n=13) and docosanoyl alcohol (n=21) were used to as starting materials instead of hexadecanol. Further, as shown in FIG. 2, the procedure set forth above was also used to synthesize hexadecyl thiophosphocholine, except that thiophosphoryl chloride was used instead of phosphoryl chloride. The expected molecular ion and the corresponding mass spectral results for each synthesized phosphocholine or thiophosphocholine derivatives were determined using mass spectral analysis. The results are shown below in Table 1.