反应详情

A mixture of {1-[(1-benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-cyclopropyl}-acetic acid methyl ester (5 mg, 0.0089 mmol), 2 M NaOH (3 mL), MeOH (3 mL) and THF (3 mL) was stirred at r.t. for 2 days, then concentrated to approximately one-third of its original volume. 1 M HCl was added until pH was about 3, and the resulting suspension was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (5-90% EtOAc/hexanes+1% AcOH). The product isolated was dissolved in saturated NaHCO3 and washed several times with ether. The aqueous layer was acidified to pH about 3, and the resulting suspension was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated to give 2.3 mg of the title compound as a yellow solid. MS: (+) m/z 547.35 (M+1).

1. concentrationconcentrated to approximately one-third of its original volume
2. addition1 M HCl was added until pH was about 3
3. extractionthe resulting suspension was extracted with EtOAc
4. dry with materialThe organic layer was dried over MgSO4
5. concentrationconcentrated
6. customThe crude product was purified by silica gel chromatography (5-90% EtOAc/hexanes+1% AcOH)
7. customThe product isolated
8. washwashed several times with ether
9. extractionthe resulting suspension was extracted with CH2Cl2
10. dry with materialThe organic layer was dried over MgSO4
11. concentrationconcentrated