Isopropanol → (S)-methyl 2-(6-((S)-1,2-dihydroxyethyl)-2-(4-(4-fluorophenoxy)phenyl) pyrimidine-4-carboxamido)propanoate

Participants

Reaction Steps

To a warmed milky suspension of (S)-methyl 2-(2-(4-(4-fluorophenoxy)phenyl)-6-vinylpyrimidine-4-carboxamido)propanoate (0,407 g, 0.966 mmol) in iPrOH (5 mL) and water (5 mL) was added AD-Mix-α (1.328 g). After stirring 2.5 hours the reaction mixture was partitioned between 25 mL water and 50 mL EtOAc. The organic layers were isolated and the aqueous layer extracted once more with 25 mL EtOAc. The combined organic layers were dried over Na2SO4, filtered, and evaporated in vacuo. The residue was chromatographed over silica gel using 50-100% EtOAc in hexanes. The product fractions were evaporated in vacuo to give (S)-methyl 2-(6-((S)-1,2-dihydroxyethyl)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxamido)propanoate (Compound Example No. 14) as a cream-colored solid (0.236 g, 0.518 mmol, 54% yield). 1H NMR (400 MHz, DMSO-d6): 9.39 (1 H, d, J=7.9 Hz), 8.64 (2 H, d, J=9.0 Hz), 8.00 (1 H, s), 7.33-7.25 (2 H, m), 7.22-7.16 (2 H, m), 7.13 (2 H, d, J=9.0 Hz), 5.82 (1 H, d, J=5.3 Hz), 4.83 (1 H, t, J=6.1 Hz), 4.72-4.60 (2 H, m), 3.85-3.77 (1 H, m), 3.72-3.63 (4 H, m), 1.49 (3 H, d, J=7.2 Hz); LC/MS: m/z=456.1 [M+H]+.

Provenance & Evidence