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

Participants

Reaction Steps

A sample of 6-phosphocholinehexanoic acid in dimethylformamide is stirred at room temperature for 5 min. To this mixture, approximately a three fold molar excess of p-nitrophenyl trifluoroacetate is added. While stirring the resulting mixture, approximately a 2 fold molar excess of 2,6-lutidine is added and the mixture is stirred until the 6-phosphocholinehexanoate completely dissolves. The reaction mixture is stirred at room temperature for an additional 6 hours. Afterwards, an aliquot of ethyl ether is added to the reaction mixture to precipitate p-nitrophenyl 6-(O-phosphocholine)hydroxyhexanoate from solution. The supernatant is decanted and the oily product is dissolved in acetonitrile and is precipitated again with ether. After the removal of solvent traces, p-nitrophenyl 6-(O-phosphocholine)hydroxyhexanoate is obtained.

Provenance & Evidence