Hydrochloric Acid → HCID 118307879, compound

Participants

Reaction Conditions

Reaction Steps

The 1.86 mL of 1M sodium hydroxide (74 mg, 1.86 mmol) was added to a solution (S)-isopropyl 2-(tert-butoxy)-2-(4-(4-ethyl-4-methylpiperidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (128 mg, 0.207 mmol) in ethanol (2 mL) and stirred for 24 h at 90° C. An additional 0.8 mL sodium hydroxide was added and the reaction was continued for 24 h. The reaction mixture was neutralized with 1N HCl solution, extracted with EtOAc, and the organic layer was washed with brine, and dried (MgSO4). The crude material was purified by prep HPLC to give (S)-2-(tert-butoxy)-2-(4-(4-ethyl-4-methylpiperidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2,6-dimethylpyridin-3-yl)acetic acid 116 mg (97%) as a mixture of diastereomers. 1H NMR (500 MHz, DMSO-d6) δ 7.38-7.35 (m, 2H), 7.20-7.18 (m, 1H), 7.13 (t, J=9.1 Hz, 2H), 7.03-7.00 (m, 3H), 5.85 (s, 1H), 4.27-4.18 (m, 2H), 3.52 (br. s, 2H), 3.27-3.21 (m, 1H), 3.04 (t, J=6.6 Hz, 2H), 2.84-2.97 (m, 1H), 2.43 (s, 3H), 2.19-2.14 (br. s, 1H), 2.05 (s, 3H), 1.96-1.91 (m, 1H), 1.49-1.38 (m, 1H), 1.29-1.23 (m, 1H), 1.17-1.12 (m, 1H), 1.12 (br. s, 9H), 1.01-0.99 (m, 1H), 0.75-0.72 (m, 3H), 0.54 (br. s, 3H). UPLC (M+H)=577.5.

Provenance & Evidence