Sodium ethoxide → HCID 54729998, compound

HRID 2364230Notes

Reaction equation

HRID 2364230 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]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 42637837HCID 42637837, compound

Product 1

HCID 54729998HCID 54729998, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperaturewarmed
  2. customSolvents were removed in vacuo
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-69ed53e559d34fe39b2a12952fc3806b
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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