p-Toluenesulfonic acid → HCID 15058114, compound

Participants

Reaction Steps

76.8 g (0.176 mol) of t-butyl (3S,4S)-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-azetidinecarbamate are dissolved in 500 ml of tetrahydrofuran and 350 ml of water and the solution is heated to 60° C. for 24 hours with 13.0 g of p-toluenesulphonic acid. The mixture is cooled, neutralized with 10% aqueous potassium bicarbonate solution and evaporated. The residue is taken up in 300 ml of dioxan and treated with 21.8 g (0.1 mol) of di-t-butyl dicarbonate and 7.63 g of potassium carbonate. The mixture is stirred at room temperature for 24 hours and filtered. The solvent is then removed by evaporation. The crude product is recrystallized from acetonitrile. 61.3 g (88%) of t-butyl (3S, 4S)-1-(2,4-dimethoxybenzyl)-4-[(R)-1,2-dihydroxyethyl]-2-oxo-3-azetidinecarbamate are obtained.

Provenance & Evidence