Sodium Hydroxide → (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-methoxyphenethoxy)phenyl)-2,6-dimethylpyridin-3-yl)acetic acid

Participants

Reaction Steps

A mixture of (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-methoxyphenethoxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (0.032 g, 0.053 mmol) and 1M NaOH (0.159 ml, 0.159 mmol) in EtOH (2 mL) was refluxed for 4 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-methoxyphenethoxy)phenyl)-2,6-dimethylpyridin-3-yl)acetic acid (0.0257 g, 0.045 mmol, 84% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.27-7.23 (m, 2H), 7.14 (dd, J=8.5, 2.0 Hz, 1H), 7.09-7.04 (m, 1H), 7.01-6.96 (m, 2H), 6.93-6.88 (m, 2H), 6.00 (br. s., 1H), 4.26-4.17 (m, 2H), 3.83 (s, 3H), 3.57 (br. s., 1H), 3.10 (t, J=7.1 Hz, 2H), 2.93 (br. s., 1H), 2.64 (s, 3H), 2.34 (br. s., 1H), 2.21 (s, 3H), 2.16-2.01 (m, 1H), 1.68-1.47 (m, 2H), 1.40-1.28 (m, 2H), 1.25 (s, 9H), 0.88 (br.s., 3H), 0.68 (br. s., 3H). LCMS (M+H)=575.4.

Provenance & Evidence