反应详情

A mixture of 7-(2,4-dimethoxy-benzyl)-4-hydroxy-8-oxo-5,6,7,8-tetrahydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (19 mg, 0.051 mmol), β-alanine (605 mg, 6.79 mmol), and NaOMe solution (10 mL, 5.11, 0.5 M in MeOH) was refluxed for 16 h. After the mixture was cooled to r.t., solvent was evaporated in vacuo. The residue was partitioned between EtOAc and water, and 1 M HCl was added with vigorous stirring until pH about 1. The organic layer was dried over MgSO4 and concentrated. The crude was first purified by silica gel chromatography (5-80% EtOAc/hexanes+2% AcOH), and the product isolated was then dissolved in saturated NaHCO3. The aqueous solution was washed with ether, acidified to pH about 1 with 4 M HCl, and the resulting precipitate was collected by filtration and dried under vacuum to give 7.3 mg of the title compound. MS: (+) m/z 430.27 (M+1).

1. temperaturewas refluxed for 16 h
2. customsolvent was evaporated in vacuo
3. customThe residue was partitioned between EtOAc and water, and 1 M HCl
4. additionwas added
5. dry with materialThe organic layer was dried over MgSO4
6. concentrationconcentrated
7. customThe crude was first purified by silica gel chromatography (5-80% EtOAc/hexanes+2% AcOH)
8. customthe product isolated
9. washThe aqueous solution was washed with ether
10. filtrationthe resulting precipitate was collected by filtration
11. customdried under vacuum