Trifluoroacetic acid → (S)-N-((R)-1,2,3,4-Tetrahydronaphthalen-1-yl)-7-(((3S,5S)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)amino)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

Participants

Reaction Steps

To a solution of (S)-tert-butyl 7-(((3S,5S)-1-(tert-butoxycarbonyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)amino)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (150 mg, 0.20 mmol) in CH2Cl2 (2.2 mL) was added TFA (303 μL, 3.93 mmol). The resulting solution was stirred at room temperature for 1 h. Additional TFA (303 μL, 3.93 mmol) was added. The reaction mixture was stirred for 2 h, then quenched carefully with sat. aq. NaHCO3 solution and poured into a separatory funnel containing EtOAc. The layers were separated, and the aqueous layer was extracted with EtOAc (3×). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (111 mg, 100%) as a tan solid. MS (ESI+) m/z 564.4 (M+H)+.

Provenance & Evidence