反应详情

Sodium metaperiodate (749 mg., 3.5 millimole) is added to a turbid solution of 7-[2-(3-hydroxyoctyl)-4-oxo-3-thiazolidinyl]heptanoic acid (1.24 g., 3.44 millimole) in methanol-water (5:4; v:v; 18 ml.) cooled in an ice bath (0° to 5° C.). After removing the cooling bath, the reaction mixture is stirred at ambient temperature for 16 hours. Precipitated solid is removed by filtration. The filtrate is diluted with cold water and extracted twice with chloroform. The combined organic extract is washed with saturated aqueous brine, dried over magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo leaves an oily residue which is applied to a silica gel column (20 g.) with chloroform. Elution with chloroform-acetic acid (25:1; v:v; 310 ml.) gives an impure forerun which is discarded. Continued elution with the same eluant (330 ml.) provides the title compound as a plae yellow oil (750 mg., 58%); pmr (CDCl3) δ 0.88 (3H, t), 4.47 (H, m) and 7.76 (2H, s, D2O exchangeable). Anal. Calcd. for C18H33NO5S: N, 3.73. Found: N, 3.37.

1. temperaturecooled in an ice bath (0° to 5° C.)
2. customAfter removing the cooling bath
3. customPrecipitated solid
4. customis removed by filtration
5. additionThe filtrate is diluted with cold water
6. extractionextracted twice with chloroform
7. extractionThe combined organic extract
8. washis washed with saturated aqueous brine
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. customEvaporation of the filtrate in vacuo
12. customleaves an oily residue which
13. washElution with chloroform-acetic acid (25:1; v:v; 310 ml.)
14. customgives an impure forerun which
15. washContinued elution with the same eluant (330 ml.)