Synthesis of sulfate esters of lithocholic acid, glycolithocholic acid, and taurolithocholic acid with sulfur trioxide-triethylamine.
The facile synthesis of lithocholic acids sulfates by a procedure that produced the desired products in over 90% yield is described. Lithocholic acid sulfate and glycolithocholic acid sulfate were synthesized by reacting lithocholic acid or glycolithocholic acid with sulfur trioxide-triethylamine complex in dimethylformamide for 0.5-1 hr. Taurolithocholic acid sulfate was obtained by conjugating lithocholic acid sulfate with taurine in dimethylformamide at 90 degrees C for 0.5 hr. The one-pot synthesis of taurolithocholic acid sulfate starting from lithocholic acid is also described. This procedure, which generated lithocholic acid sulfate in situ, produced taurolithocholic acid sulfate in 98% yield, compared to an overall yield of less than 10% obtained by previously published procedures.
D002793:Cholic Acids / Q000031:analogs & derivatives; D002855:Chromatography, Thin Layer; D005021:Ethylamines; D006000:Glycocholic Acid / Q000031:analogs & derivatives; D007202:Indicators and Reagents; D008095:Lithocholic Acid / Q000031:analogs & derivatives; D008722:Methods; D013329:Structure-Activity Relationship; D013464:Sulfuric Acids / Q000138:chemical synthesis*; D013656:Taurocholic Acid / Q000031:analogs & derivatives
D002793:Cholic Acids; D005021:Ethylamines; D007202:Indicators and Reagents; D013464:Sulfuric Acids; D013656:Taurocholic Acid; D008095:Lithocholic Acid; D006000:Glycocholic Acid