Chloroform → 7-[2-(3-Hydroxyoctyl)-1,4-dioxo-3-thiazolidinyl]heptanoic Acid

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Reaction Steps

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.

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