Triethylamine → (+,-) Cis Propane-2-sulfonic Acid [2-(4-methanesulfonylamino-phenyl)-cyclopentyl]-amide

Participants

Reaction Conditions

Reaction Steps

(+,−) Cis propane-2-sulfonic acid [2-(4-amino-phenyl)-cyclopentyl]-amide (73 mg, 0.26 mmol, prepared in example 23) was dissolved in 10 mL of methylene chloride and cooled to 0° C. under nitrogen. Triethylamine was added (40 uL, 0.28 mmol) followed by methanesulfonyl chloride (22 uL, 0.28 mmol) and after stirring 15 min the ice bath was removed and stirring continued. After 4 hours an additional 10 uL of methanesulfonyl chloride was added and stirring continued overnight. The reaction was concentrated in vacuo and purified by radial chromatography eluting with 99:1 methylene chloride:methanol and slowly increasing the percentage of methanol. The appropriate fractions were dried to 25 mg (27%) of the title compound as an off-white solid. The NMR was consistent with the assigned structure.

Provenance & Evidence