Reaction Steps
To a solution of (S)-2-((S)-3-acetamido-3-((R)-sec-butyl)-2-oxopyrrolidin-1-yl)-N-((1S,2S)-1-((R)-8-(allyloxy)-2-benzhydryl-1,2,3,4-tetrahydroisoquinolin-3-yl)-3-(3,5-difluorophenyl)-1-hydroxypropan-2-yl)-4-phenylbutanamide (Step 3 (A), 50 mg) in MeOH (5 mL) was added a catalytic amount of Pd on activated charcoal (10 wt %) and acetic acid (0.2 mL). The reaction mixture was put on hydrogenator at 50 psi for 3.5 h. The mixture was then filtered and concentrated in vacuo and purified by silica gel Flash chromatography to give 30 mg of the title compound of compound 3 (74% yield). 1H NMR (CD3OD, 500 MHz) δ 0.76 (3H, d, J=5 Hz), 0.97-1.00 (3H, m), 1.04-1.07 (4H, m), 1.64-1.69 (2H, m), 1.78-1.85 (2H, m), 1.94 (1H, s), 1.97-2.03 (4H, m), 2.06-2.20 (3H, m), 2.38-2.44 (1H, m), 2.53-2.59 (1H, m), 2.78 (1H, dd, J=10, 15 Hz), 2.96 (1H, m), 3.10-3.20 (2H, m), 3.26-3.31 (2H, m), 3.42 (1H, dt, J=5, 10 Hz), 3.97 (2H, t, J=5 Hz), 4.01-4.05 (2H, m), 4.12 (1H, m), 4.22 (1H, dt, J=5, 10 Hz), 4.32 (1H, d, J=15 Hz), 6.75 (1H, m), 6.80 (2H, d, J=10 Hz), 6.92 (2H, d, J=5 Hz), 6.95 (2H, d, J=10 Hz), 7.10-7.19 (4H, m). MS (ESI) (M+H)+ 719.37.
