Diethyl Ether → 6-(4-Nitrophenoxy)-6-oxohexyl 2-(trimethylazaniumyl)ethyl phosphate

Participants

Reaction Steps

A sample of 505 mg (1.7 mmol) of 6-phosphocholinehexanoic acid in 11 ml of dimethylformamide was stirred at room temperature for 5 min. To this mixture, 1.3 g (5.5 mmol) of p-nitrophenyl trifluoroacetate was added. While stirring the resulting mixture, 0.43 ml (3.7 mmol) of 2,6-lutidine was added and the mixture was stirred until the 6-phosphocholinehexanoate completely dissolved. The reaction mixture was stirred at room temperature for an additional 6 hours. Afterwards, a 150 ml aliquot of ethyl ether was added to the reaction mixture to precipitate p-nitrophenyl 6-(O-phosphocholine)hydroxyhexanoate from solution. The supernatant was decanted and the oily product was dissolved in 5 ml of acetonitrile and precipitated again with ether. After the removal of solvent traces, 571 mg of p-nitrophenyl 6-(O-phosphocholine)hydroxyhexanoate was obtained at a yield of about 80%. The overall synthesis produced a yield of about 27%.

Provenance & Evidence