p-Toluenesulfonic acid → HCID 14206137, compound

Participants

Reaction Steps

240.0 mg of p-toluenesulfonic acid were added to a solution of 2.753 g of (2S, 3R)-2-(triphenylmethoxymethyl)tetrahydropyran-3-yl N-heptadecylcarbamate (prepared as described in Preparation 27) dissolved in 55 ml of methanol, and the mixture was heated under reflux for 1 hour. At the end of this time, the reaction mixture was cooled, and 352.6 mg of sodium bicarbonate were added. The methanol was then removed by distillation under reduced pressure, and ethyl acetate was added. Insoluble materials were filtered off, and the filtrate was concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 55 g of silica gel. 1.476 g of the title compound was obtained from those fractions eluted with mixtures of hexane and ethyl acetate ranging from 2:1 to 1:1 by volume in the form of crystals melting at 92.0°-93.5° C. (after recrystallisation from diethyl ether).

Provenance & Evidence