Triphenylphosphine → HCID 118307766, compound

Participants

Reaction Steps

To a stirred solution of (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-hydroxyphenyl)-2,6-dimethylpyridin-3-yl)acetate (50 mg, 0.107 mmol), 2-(5-methylthiophen-2-yl)ethanol (76 mg, 0.533 mmol) and Ph3P (139 mg, 0.533 mmol) in THF (2 mL) was added DIAD (0.104 mL, 0.533 mmol) at rt. After 18 h, mixture was filtered to remove polymer, concentrated and treated with 1N NaOH (0.854 mL, 0.854 mmol) in MeOH (1 mL) at 75° C. for 16 h. Mixture was then cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-5-(4-(2-(5-methylthiophen-2-yl)ethoxy)phenyl)pyridin-3-yl)acetic acid (13 mg, 0.023 mmol, 21.57% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.20 (d, J=8.8 Hz, 1H), 7.10-6.91 (m, 4H), 6.73 (d, J=3.3 Hz, 1H), 6.63 (br. s., 1H), 5.82 (s, 1H), 4.29-4.07 (m, 3H), 3.26 (br. s., 1H), 3.17 (t, J=6.1 Hz, 1H), 2.43 (s, 3H), 2.38 (s, 3H), 2.15 (br. s., 1H), 2.05 (s, 3H), 1.28 (br. s., 2H), 1.17 (d, J=16.5 Hz, 1H), 1.11 (s, 9H), 1.07-0.94 (m, 2H), 0.83 (br. s., 3H), 0.60 (br. s., 3H). LCMS (M+H)=565.3.

Provenance & Evidence