HCID 22261102, compound → HCID 135550701, compound

Participants

Reaction Steps

A mixture of 2-(4-{2-[2-(4-benzyloxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid (0.238 g, 0.490 mmol) and 5% palladium on carbon (0.10 g) in tetrahydrofuran (10 mL) and methanol (10 mL) was purged successively with nitrogen then hydrogen, and then stirred under a hydrogen balloon at room temperature for 18 h. The reaction mixture was filtered through hyflo and solvent was removed from the filtrate in vacuo to give an oil which was dissolved in CH2Cl2 and dried (MgSO4). The solvent was removed in vacuo to give a crude oil which was purified by flash chromatography (9/1 CH2Cl2/MeOH) to afford 0.072 g (37%) 2-(4-{2-[2-(4-hydroxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid. 1H NMR (500 MHz, DMSO-d6) δ 10.08 (bs, 1H), 7.70 (d, 2H, J=8.60 Hz), 6.84-6.72 (m, 6H), 4.08 (t, 2H, J=6.65 Hz), 2.83 (t, 2H, J=6.65 Hz), 2.28 (s, 3H), 1.33 (s, 6H); MS (ES+) Calc'd for C22H23NO6: Found m/e 398 (M+1, 100%)

Provenance & Evidence