Beta-Alanine → 3-[(4-Hydroxy-7-phenoxy-1-phenyl-isoquinoline-3-carbonyl)-amino]-propionic acid

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Reaction Steps

A mixture of 4-hydroxy-7-phenoxy-1-phenyl-isoquinoline-3-carboxylic acid methyl ester (46 mg, 0.12 mmol), β-alanine (552 mg, 6.2 mmol) and NaOMe (9.3 mL, 4.65 mmol, 0.5 M in MeOH) was refluxed for 16 h. After cooling to r.t., the solvent was evaporated. The residue was partitioned between EtOAc (50 mL) and water (50 mL). 1 M HCl was added with stirring until pH was ˜2. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (0-35% EtOAc/hexanes+2% AcOH) to give 47 mg of the title compound as a light yellow solid. MS: (+) m/z 429.13 (M+1).

Provenance & Evidence