HCID 10869127, compound → HCID 10999379, compound

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).

1. dissolutionto redissolve the cloudy precipitate which
2. customformed
3. temperaturebecame warm
4. customa precipitate slowly formed
5. extractionthe mixture extracted with ethyl acetate (3×20 ml)
6. washThe combined ethyl acetate extracts were washed with saturated aqueous sodium sulfite solution (2×20 ml), water (3×20 ml) and brine (20 ml)
7. dry with materialdried (MgSO4)
8. customEvaporation of the solvent under reduced pressure
9. customgave a yellow oil, which
10. customwas purified by silica-gel chromatography
11. washeluting with ethyl acetate/hexane mixtures
12. washby high-pressure silica-gel chromatography, eluting with 60% ethyl acetate/hexane

ORD record

ord-a4f9c33b2a844854aad1524e14772b45

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06022976