Hydrochloric Acid → HCID 117736906, compound

Participants

Reaction Conditions

Reaction Steps

(E)-Ethyl 3-(5-(benzylthio)-2-iodophenyl)acrylate (0.225 g, 0.265 mmol) was added to a vial and dissolved in acetonitrile (2.494 ml). Acetic acid (0.095 ml) and water (0.062 ml) were added and the vial was cooled to 0° C. 1,3-dichloro-5,5-dimethylhydantoin (0.057 g, 0.292 mmol) was then added as a solid in one portion while 0° C. was maintained. After 20 min. LC/MS showed mass corresponding to sulfoxide (mono-oxidation) along with sulfonyl chloride. After 1 hr. an additional 0.2 equiv (10 mg) of hydantoin was added. After an additional 20 min. the oxidation was complete. Solid sodium bisulfite was added and the reaction was diluted with EtOAc and water and stirred for 5 min. The organic layer was separated, the aq. re-extracted 2× with EtOAc, and the organic layers combined. After washing with brine, drying with Na2SO4, and concentrating, the crude residue was brought up in 1.5 mL of DCM and treated with 3-aminoisoxazole (0.039 ml, 0.530 mmol) and pyridine (0.107 ml, 1.326 mmol) After 45 min, the reaction was poured into 1N HCl and extracted 2× with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentrated to give an orange solid that was purified by MPLC (25 g puriflash, 25-85% EtOAC:Heptanes) to give (E)-ethyl 3-(2-iodo-5-(N-(isoxazol-3-yl)sulfamoyl)phenyl)acrylate (0.043 g, 0.096 mmol, 36.2% yield) as a white solid. m/z (ESI) 447.0 (M−H)−.

Provenance & Evidence