Hydrochloric Acid → HCID 10127704, compound

Participants

Reaction Steps

Ethyl [(1S)-5-(2-{5-methyl-2-[4-(4-morpholinyl)phenyl]-1,3-oxazol-4-yl}ethoxy)-2,3-dihydro-1H-inden-1-yl]acetate (0.058 g, 0.12 mmol) was dissolved in EtOH (1 mL), and LiOH.H2O (0.025 g, 0.6 mmol) was added. Water (1 mL) was added, followed by THF was added until the cloudy solution became clear. The resulting mixture was stirred overnight at rt. HCl (2 N) was added to adjust the pH to 2, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried, filtered and evaporated. The residue was purified by preparative HPLC to obtain [(1S)-5-(2-{5-methyl-2-[4-(4-morpholinyl)phenyl]-1,3-oxazol-4-yl}ethoxy)-2,3-dihydro-1 H-inden-1-yl]acetic acid (0.038 g, 0.08 mmol) in 70% yield. 1H NMR ((CDCl3) δ 1.8 (m, 1H), 2.4 (m, 3H), 3.0 (t, 2H), 3.3 (m, 4H), 3.5 (m, 1H), 3.9 (m, 4H), 4.2 (t, 2H), 6.7 (m, 1H), 6.8 (s, 1H), 6.9 (d, 2H), 7.1 (d, 1H), 7.9 (d, 2H); MS (ES) 463 (M+1)+.

Provenance & Evidence