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

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Reaction Steps

A mixture of 1-cyano-4-hydroxy-7-phenyl-isoquinoline-3-carboxylic acid methyl ester (46 mg, 0.15 mmol), β-alanine (674 mg, 7.57 mmol) and NaOMe (327 mg, 6.05 mmol) in 2-methoxyethanol (12 mL) was refluxed for 1.5 h. After the mixture was cooled to r.t., solvent was evaporated. The residue was partitioned between EtOAc (50 mL) and water (50 mL). 1 M HCl was added with vigorous stirring until pH was ˜2. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (0-60% EtOAc/hexanes+2% AcOH) to give 30 mg of the title compound as a pale pink solid. MS: (−) m/z 360.07 (M−1).

Provenance & Evidence