Diphenylpropionic acid → N-Methoxy-N-methyl-3,3-diphenyl-propionamide

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Reaction Steps

To a solution of 3,3-diphenylpropionic acid ((CAS RN: [606-83-7]), 1.5 g) in DMF (17 mL) was added TBTU (3.0 g) and Et3N (2.8 mL) at 0° C. The reaction mixture was stirred at rt for 10 min and again was cooled down to 0° C. N,O-dimethylhydroxylamine hydrochloride (0.78 g) was added and the mixture was stirred at rt for 2 days. A saturated solution of NaHCO3 and TBME were added, the phases were separated and the inorganic one was extracted with TBME. The combined organic layers were washed with 1M KHSO4 followed by brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1) to yield the title compound as a light brown oil (1.5 g, 84%), MS (ESI+): m/z=270.2 ([M+H]+).

Provenance & Evidence