Benzyl Bromide → Benzyl rel-({(3r,4r)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]-4-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-3-yl}oxy)acetate

Participants

Reaction Steps

The title compound was synthesized in similar fashion to rel-N-[2-({(3R,4R)-4-(benzyloxy)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide, benzyl bromoacetate was substituted for benzyl bromide, as well as benzylcarbamate deprotection was accomplished with H2 gas (1 atm), 10% Palladium/Carbon in methanol, and was isolated as a white solid. 1H-NMR (CD3OD) δ: 1.17-1.25 (m, 1H), 1.50-1.67 (m, 2H), 1.80-1.94 (m, 2H), 2.13-2.25 (m, 1H), 2.44 (dd, J=10.5, 4.2 Hz, 1H), 2.61-2.74 (m, 3H), 2.84 (dd, J=9.9, 6.0 Hz, 1H), 3.25 (dd, J=10.2, 6.3 Hz, 1H), 3.35-3.46 (m, 3H), 3.85 (s, 3H), 3.82-3.93 (m, 1H), 4.05-4.14 (m, 3H), 4.18-4.29 (m, 3H), 5.11 (s, 2H), 6.63 (d, J=9.0 Hz, 1H), 6.74 (d, J=7.8 Hz, 1H), 7.20-7.38 (m, 5H), 7.51 (t, J=7.8 Hz, 1H), 7.70-7.75 (m, 2H), 7.96 (d, 7.8 Hz, 1H), 8.06 (s, 1H). MS m/z: 670 (M+1).

Provenance & Evidence