Isopropylamine → N-[7-(isopropylamino-methyl)-chroman-4-yl]-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide

Participants

Reaction Conditions

Reaction Steps

N-(7-Hydroxymethyl-chroman-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide (Step A) (0.050 g, 0.010 mmol) and DIEA (0.038 g, 0.030 mmol) were dissolved in THF (1.5 mL). The solution was cooled to 0° C. and methanesulfonic anhydride (0.023 g, 0.014 mmol) was added. After the reaction was stirred for 3.5 h, isopropylamine (0.14 g, 2.3 mmol) was added and the solution was stirred at RT overnight. The reaction was diluted with CHCl3 and washed with brine. The aqueous phase was extracted once with CHCl3. The organic phases were combined, dried over MgSO4, filtered, and concentrated in vacuo to provide a residue which was purified by column chromatography (silica, 0.2% TEA in acetone) to provide the title compound. MS (ESI) m/z 558 (M+H)+.

Provenance & Evidence