tert-Butyl ((S)-1-(((S)-3,3-dimethyl-1-((S)-7-nitro-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-1-oxobutan-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate → tert-Butyl ((S)-1-(((S)-1-((S)-7-amino-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate

Participants

Reaction Steps

To a pressure flask containing 10% Pd/C (240 mg, 0.23 mmol) was added a solution of tert-butyl ((S)-1-(((S)-3,3-dimethyl-1-((S)-7-nitro-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-1-oxobutan-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate (1.46 g, 2.25 mmol) in MeOH (11.2 mL). The resulting reaction mixture was stirred under H2 at 15 psi for 3 h and then filtered through a pad of CELITE® rinsing with EtOAc. The filtrate was concentrated in vacuo and redissolved in CH2Cl2. The solution was filtered through a 0.45 μM PTFE filter and concentrated in vacuo to give the title compound (1.28 g, 92%) as a yellow solid. MS (ESI+) m/z 620.4 (M+H)+.

Provenance & Evidence