Sodium ethoxide → HCID 54729998, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C:6]([N:8]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:9]1[C:10]([C:23](OCC)=[O:24])=[N:11][CH:12]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:14]=1)=[O:7])[CH3:2].[O-]CC.[Na+]>C(O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:13]2[CH:14]=[C:9]3[C:10]([C:23]([OH:24])=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:32])[C:6](=[O:7])[N:8]3[CH2:28][CH:29]([CH3:31])[CH3:30])=[N:11][CH:12]=2)=[CH:17][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cold (0° C.) solution of ethyl 3-[[3-(ethyloxy)-3-oxopropanoyl](2-methylpropyl)amino]-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (309 mg, 0.70 mmol) in ethanol (20 mL) was added sodium ethoxide (104 mg, 1.53 mmol). The resultant solution was warmed to room temperature as the bath warmed and stirred overnight. Solvents were removed in vacuo and the residue was taken up in water. The pH was adjusted to 5 with 1 N HCl (aq) and the aqueous layer extracted with ethyl acetate. The organics were dried over sodium sulfate filtered and concentrated to give ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(2-methylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (279 mg, 99%) as a clear foam. 1H NMR (CDCl3) δ 13.77 (broad, 1 H), 8.49 (s, 1 H), 7.23 (s, 1 H), 7.15 (dd, J=8.4, 5.6 Hz, 2 H), 7.04 (dd, J=8.8, 8.4 Hz, 2 H), 4.50 (q, J=7.2 Hz, 2 H), 4.11 (s, 2 H), 3.95 (broad, 2 H), 1.97 (m, 1 H), 1.45 (t, J=7.2 Hz, 3 H), 0.87 (d, J=6.4 Hz, 6 H); HRMS calcd for C22H24FN2O4 399.1720 (M+H); found 399.1720.