Trifluoroacetic acid → N-{(1S)-1-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylcarbonyl]-2,2-dimethylpropyl}-1H-indole-2-carboxamide

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl (1S,4S)-5-[N-(1H-indol-2-ylcarbonyl)-3-methyl-L-valyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (40.5 g, 89.2 mmol) in CH2Cl2 (300 mL) was added TFA (75 mL) at 0° C. The mixture was stirred at room temperature for 18 h. The reaction was quenched with 1N NaOH while adjusting the pH of the solution to 8-9. The reaction was then extracted with CH2Cl2 (3×500 mL), dried over Na2SO4, filtered, and concentrated to yield the crude product. LCMS (m/z): 355.3 (M+H).

Provenance & Evidence