Iodine → (R,R) Propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Participants

Reaction Conditions

Reaction Steps

(+,−) Cis-propane-2-sulfonic acid (2-phenyl-cyclopentyl)-amide (1.8 g, 6.7 mmol, prepared in example 16) was dissolved in 20 mL of glacial acetic acid and 0.7 mL (7.1 mmol) of concentrated sulfuric acid added followed by 2 mL of water. To this solution was added periodic acid (0.35 g, 1.6 mmol) and iodine (0.77 g, 3.0 mmol). The resulting mixture was heated to 60° C. for 3 hours. The reaction was cooled to room temperature and 20 mL of a 10% aqueous solution of sodium bisulfite was added. The product was extracted into ethyl acetate then washed with water, dilute sodium bicarbonate, and dried over magnesium sulfate. Filtered and concentrated in vacuo to 2.2 g of crude yellow oil. This oil was purified by reverse phase chromatography to give 341 mg (13%) of the title compound as a white solid. The NMR was consistent with the assigned structure.

Provenance & Evidence