Lithium Hydroxide → 4-Chloro-3'-((2-cyclopentyl-1-oxoisoindolin-5-yloxy)-methyl)biphenyl-3-carboxylic acid

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Reaction Steps

Crude methyl 4-chloro-3′-((2-cyclopentyl-1-oxoisoindolin-5-yloxy)methyl)biphenyl-3-carboxylate (109 mg, 0.23 mmol) was dissolved in tetrahydrofuran (17 mL) and 2M LiOH (0.57 mL, 1.15 mmol) was added and the mixture was heated at reflux for 3 h. The solvent was evaporated and the residue was dissolved in water and neutralized using 2M HCl. The aqueous layer was extracted with ethyl acetate and the organic layer was dried over anhydrous Na2SO4. The solvent was evaporated in vacuo to obtain the crude acid as a yellow solid. The crude residue was purified using automated prep-HPLC to yield the desired compound (48 mg, 46%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.18 (s, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.65-7.41 (m, 6H), 7.05 (d, J=8.5 Hz, 1H), 6.99 (s, 1H), 5.16 (s, 2H), 4.74 (m, 1H), 4.30 (s, 2H), 1.97 (m, 2H), 1.76-1.59 (m, 6H). HRMS: calcd. for C27H24CINO4 [M+H]+ 462.1467; found 462.1468.

Provenance & Evidence