Ethanolamine → Monosodium 2-(2-hydroxy-3-tetradecyloxypropylamino)ethyl phosphate

Participants

Reaction Steps

A 300-ml flask equipped with a stirrer was charged with 5.13 g (14.8 mmol) of 3-(2-hydroxyethylamino)-1-tetradecyloxy-2-propanol prepared from tetradecyl glycidyl ether and ethanolamine in the same manner as in Preparation Example 14, and 70 mol of tetrahydrofuran, 1.95 g (16.9 mmol) of 85% phosphoric acid and 3.54 g (30.7 mmol) of P2O5 were added thereto. The resultant mixture was stirred at 65° C. for 10 hours. After cooling the mixture to room temperature, 0.56 g of water was added to the mixture, stirring was conducted for 30 minutes, 5.0 g of 48% aqueous NaOH were added further. After concentrating the resultant reaction mixture under reduced pressure, the resultant residue was subjected to extraction with ethanol by means of a Soxhlet's extractor. The resultant extract was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel, thereby obtaining 2.32 g (yield: 34.9%) of the title compound monosodium (IIa-14).

Provenance & Evidence