Hydrochloric Acid → 5-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-furan-2-carboxylic acid methyl ester

Participants

Reaction Steps

[1-(5-Phenethylcarbamoyl-furan-2-sulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.15 g, 0.3 mmol) was suspended in a 4M solution of HCl in Dioxane (5 ml). The resulting suspension was stirred at room temperature for 3 hours. After this time the solution was concentrated under vacuum and the resulting residue dissolved in THF (10 ml). To this solution was added diisopropylethylamine (0.3 ml, 1.6 mmol) was added in one portion, followed by the drop wise addition of acryloyl chloride (0.03 ml, 0.38 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was diluted with DCM (20 ml) and washed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml). The organic layer was separated, dried (MgSO4), filtered, concentrated and the resulting residue was purified by flash column chromatography (elution: 50% EtOAc, 50% heptane) to give the title compound (0.01 g, 2% yield) as a white solid.

Provenance & Evidence