Lithium Hydroxide → (2S)-2-[5-(6-benzyloxy-3-pyridyl)-4-(4,4-dimethyl-1-piperidyl)-2,6-dimethyl-3-pyridyl]-2-tert-butoxy-acetic acid

Participants

Reaction Steps

A solution of (S)-ethyl 2-(6′-(benzyloxy)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-[3,3′-bipyridin]-5-yl)-2-(tert-butoxy)acetate (0.014 g, 0.025 mmol) and LiOH (5.99 mg, 0.250 mmol) in 9:1 EtOH/H2O (2 mL) was refluxed for 3 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(6′-(benzyloxy)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-[3,3′-bipyridin]-5-yl)-2-(tert-butoxy)acetic acid (0.0089 g, 0.017 mmol, 66.9% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 8.08 (d, J=2.2 Hz, 0.5H), 7.99 (d, J=1.7 Hz, 0.5H), 7.46-7.54 (m, 3H), 7.33-7.45 (m, 3H), 6.94 (dd, J=5.8, 8.4 Hz, 1H), 5.93 (br. s., 1H), 5.40-5.55 (m, 2H), 3.40-3.70 (m, 0.5H), 2.74-3.11 (m, 0.5H), 2.67 (s, 3H), 2.28 (s, 1.5H), 2.25 (s, 1.5H), 1.94-2.20 (m, 1H), 1.27-1.40 (m, 4H), 1.25 (s, 4.5H), 1.24 (s, 4.5H), 0.80 (br.s., 6H). LCMS (M+H)=532.4.

Provenance & Evidence