p-Toluenesulfonic acid → HCID 10834640, compound

Participants

Reaction Steps

The (S)-tert-butyl 4-((R)-1-hydroxy-2-hexadecynyl)-2,2-dimethyloxazolidine-3-carboxylate) (100 mg, 0.23 mmol) obtained in the above-described reaction was dissolved in methanol (4.4 ml); p-toluenesulfonic acid (0.8 mg, 4.6 μmol) was added to the solution, and the mixture was stirred at room temperature for 12 hours. P-toluenesulfonic acid (0.8 mg, 4.6 μmol) was added to this reaction mixture, stirred for 6 hours, heated to 60° C., and further stirred for 2 hours. Saturated sodium hydrogen carbonate was added to this reaction mixture, and the reaction was stopped; the mixture was subsequently extracted with ethyl acetate, and the organic layer was dried and filtered. The resulting filtrate was purified by column chromatography to produce tert-butyl (2S,3R)-1,3-dihydroxyoctadec-4-yn-2-ylcarbamate (85 mg, 93% yield).

Provenance & Evidence