Water → HCID 21841991, compound

Participants

Reaction Conditions

Reaction Steps

To a solution containing 61.5 g of the title compound of Step A dissolved in 1300 mL of dichloromethane under a nitrogen atmosphere was added 154 g of triphosgene portionwise with external cooling to maintain the reaction temperature at 0-20° C. The reaction mixture was then heated at reflux for approximately 24 h and then was cooled to 0° C. The reaction mixture was poured into water. The organic layer was separated and washed with water and saturated aqueous sodium chloride. The organic layer was then dried over magnesium sulfate, filtered and the filtrate was then evaporated to obtain 35.49 g of a white solid. This solid was purified by column chromatography on silica gel eluting with 2:1 hexane/ethyl acetate. Collection and evaporation of the fractions containing only the most polar component (according to thin layer chromatography on silica gel, 1:1 hexane/ethyl acetate mixture as the development solvent) yielded 12.2 g of the title compound of Step B as a white solid.

Provenance & Evidence