Trifluoroacetic acid → (+,-) Trans Propane-2-sulfonic acid {2-[4'-(2-methanesulfonylamino-ethyl)-biphenyl-4-yl]-cyclopentyl}-amide

Participants

Reaction Conditions

Reaction Steps

(+,−) Trans propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (300 mg, 0.76 mmol, prepared in example 2) and N-carbamic acid tert-butyl ester-N-methanesulfonamide-N-phenethyl-4-boronic acid (316 mg, 0.92 mmol) were dissolved in 20 mL of n-propanol and 25 mg (0.18 mmol)of potassium carbonate in 5 mL of water added. A catalytic amount of palladium acetate is added (9 mg) and the mixture refluxed at 90° C. for 4 hours. The reaction is worked up as in preparation 6. Dissolved the residue in methylene chloride and added 5 mL neat TFA and stirred overnight at room temperature. The TLC indicated the Boc protecting group had been removed and the reaction was concentrated in vacuo. Purification by silica chromatography using a Chromatotron® was achieved eluting with 95:5 methylene chloride:ethyl acetate to afford 225 mg (64%) of the title compound. The NMR was consistent with the assigned structure.

Provenance & Evidence