Sodium ethoxide → HCID 69481048, compound

Participants

Reaction Steps

To a cold (0° C.) solution of ethyl 3-{[3-(ethyloxy)-3-oxopropanoyl][3-(1-pyrrolidinylsulfonyl)propyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (275 mg, 0.488 mmol) in ethanol (5 mL) was added sodium ethoxide (347 μL, 3.09 M in ethanol, 1.07 mmol) dropwise. The reaction mixture was warmed to room temperature and stirred 10 minutes, then poured onto ice. Once the ice had melted, the mixture was diluted with water and washed with ethyl acetate. The aqueous layer was acidified with 1 N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration provided ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(1-pyrrolidinylsulfonyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.51 (s, 1 H), 7.73 (s, 1 H), 7.23 (dd, J=8.3, 5.4 Hz, 2 H), 7.02 (t, J=8.7 Hz, 2 H), 4.51 (q, J=7.1 Hz, 2 H), 4.38 (t, J=7.8 Hz, 2 H), 4.12 (s, 2 H), 3.37-3.33 (m, 4 H), 3.05 (t, J=6.5 Hz, 2 H), 2.18 (m, 2 H), 1.96-1.93 (m, 4 H), 1.48 (t, J=7.2 Hz, 3 H); MS m/z 518 (M+H)+.

Provenance & Evidence