Sodium Hydroxide → HCID 66799516, compound

Participants

Reaction Steps

50% Aqueous NaOH (0.5 mL, 0.6 mmol) was added to a solution of the crude ester (0.150 g, 0.3 mmol) in dioxane (5 mL). The reaction mixture was heated to reflux for 1 h, and then cooled to room temperature. Excess solvent was removed under reduced pressure. The residue was diluted with water and then acidified using 1M HCl. Extraction using ethyl acetate, followed by silica gel column chromatography afforded 4-chloro-4′-((2-cyclopentyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yloxy)methyl)biphenyl-3-carboxylic acid as colorless solid (0.125 g, 88%). Final HPLC purification was performed using isopropyl alcohol (IPA):H2O solvent system. 1H NMR (400 MHz, DMSO-d6): δ 8.00 (s, 1H), 7.60-7.78 (m, 2H), 7.63-7.45 (m, 5H), 7.15 (d, 1H, J=8.6 Hz)), 7.09 (d, 1H, J=8.6 Hz), 5.17 (s, 2H), 4.97-4.93 (m, 1H), 3.34 (t, 2H, J=6.1 Hz), 2.86 (t, 2H, J=6.1 Hz), 1.65-1.50 (m, 8H). LC-MS (ESI) Calcd for C28H26ClNO4 [M+H]+: 476.16. Found: 475.95. HRMS (ESI) calcd for C28H26ClNO4 [M+H]+: 476.1623. Found: 476.1621.

Provenance & Evidence