p-Toluenesulfonic acid → (4R)-4-(Propan-2-yl)-1,3-oxazolidin-2-one

Participants

Reaction Steps

A solution of (E) 3-[6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-(S), 4-dimethylhexanoyl)-4-(R)-isopropyl-2-oxazolidinone (1.3 g) and p-toluenesulphonic acid (0.6 g) in methanol (25 ml) was left at room temperature for 24 hours. The solution was diluted with methylene chloride and washed with dilute aqueous sodium bicarbonate and water, then dried and evaporated. The residue was chromatographed on silica gel, eluting with 99.2:0.8 methylene chloride methanol, to give (E) 3-[6-(1,3-dihydro-6-methoxy-4-hydroxy-7-methyl-3-oxoisobenzofuran-5-yl)]-2-(S), 4-dimethylhexanoyl)-4-(R) -isopropyl-2-oxazolidinone, mp 127°-128-C (hexane/methylene chloride).

Provenance & Evidence