HCID 10869127, compound → HCID 10999379, compound

Participants

Reaction Steps

A stirred solution of 3-(3,4-dichlorophenyl)-5-hydroxythiazolidin4-one (264 mg, prepared as in Example 1 of WO 94/13652) in methanol (5 ml) was treated with a solution of sodium periodate (852 mg) in water (10 ml). More methanol (5 ml) was added to redissolve the cloudy precipitate which formed. Ruthenium trichioride (10 mg) was added, whereupon the solution turned brown, became warm and a precipitate slowly formed. The resultant slurry was stirred for 2 hours, then water (30 ml) was added and the mixture extracted with ethyl acetate (3×20 ml). The combined ethyl acetate extracts were washed with saturated aqueous sodium sulfite solution (2×20 ml), water (3×20 ml) and brine (20 ml), then dried (MgSO4). Evaporation of the solvent under reduced pressure gave a yellow oil, which was purified by silica-gel chromatography, eluting with ethyl acetate/hexane mixtures, then by high-pressure silica-gel chromatography, eluting with 60% ethyl acetate/hexane, to give the title compound as a white solid (52 mg).

Provenance & Evidence