Thiazole → HCID 131717087, compound

Participants

Reaction Steps

A solution of 0.940 g of (2RS)-3-(N-heptadecylcarbamoyloxy)-2-(3-isoxazolyloxy)propyl 2-bromoethyl phosphate [prepared as described in Example 11(a)] and 1.06 ml of thiazole in toluene was heated on an oil bath kept at 70° C. for 4 days, whilst stirring. The solvent 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 solution thus obtained was passed over 11 ml of Amberlite (trade mark) MB 3 resin. The eluate was repeatedly passed six 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. 0.312 g of the title compound was obtained as a resinous material from the fractions eluted with a 60:35:5 by volume mixture of methylene chloride, methanol and water.

Provenance & Evidence