Acetone → HCID 19986092, compound

Participants

Reaction Steps

1(b) 1.056 g of the crude (2RS)-3-octadecyloxy-2-(2-thiazolyloxy)propyl 2-bromoethyl phosphate [prepared as described in step (a) above] was dissolved in 26 ml of a 3:5:5 by volume mixture of chloroform, isopropanol and dimethylformamide, and about 10 g of gaseous trimethylamine was introduced into the solution. The reaction mixture was then warmed, whilst stirring, for 5.5 hours on an oil bath kept at 50° C. in a reaction flask fitted with a reflux condenser cooled with dry ice and acetone. At the end of this time, the reaction mixture was cooled, and 0.355 g of silver carbonate was added. The mixture was then heated under reflux on an oil bath for 1 hour. The mixture was then cooled and concentrated by evaporation under reduced pressure. Methanol was added to the residue, and an insoluble material was filtered off. The solvent was stripped off from the filtrate, and the residue (1.07 g) was subjected to column chromatography through 25 g of silica gel. 0.690 g of the title compound was obtained as a white powder melting at 140° to 160° C. (with decomposition) from the fractions eluted with mixtures of methylene chloride and methanol ranging from 3:10 to 2:1 by volume and with methanol.

Provenance & Evidence