1-Methylimidazole → HCID 178443007, compound

Participants

Reaction Steps

A mixture of 0.900 g of (2RS)-3-(N-heptadecylcarbamoyloxy)-2-(3-isoxazolyloxy)propyl 2-bromoethyl phosphate [prepared as described in Example 11(a)], 1.14 ml of N-methylimidazole and 1.0 ml of toluene was heated on an oil bath kept at 80° C. for 15 hours, whilst stirring. The toluene was then distilled off, and the resulting residue was dissolved in 10 ml of a 95:5 by volume mixture of tetrahydrofuran and water. The resulting solution was passed through a column of 14 ml of Amberlite MB-3 resin. The eluate wa repeatedly passed two times through the same column and the column was finally washed with a 95:5 by volume mixture of tetrahydrofuran and water. The eluates and the washings were combined and concentrated by evaporation under reduced pressure. The residue was purified by medium pressure liquid chromatography using a Lobar B column. 0.656 g of the title compound was obtained as a white powder melting at 45°-46° C. from the fractions eluted with a 160:35:5 by volume mixture of methylene chloride, methanol and water.

Provenance & Evidence