Sodium ethoxide → HCID 69481048, compound

HRID 2364246Notes

Reaction equation

HRID 2364246 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][C:6]([N:8]([CH2:28][CH2:29][CH2:30][S:31]([N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)(=[O:33])=[O:32])[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.O>[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:39])[C:6](=[O:7])[N:8]3[CH2:28][CH2:29][CH2:30][S:31]([N:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)(=[O:32])=[O:33])=[N:11][CH:12]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 69481854HCID 69481854, compound

Product 1

HCID 69481048HCID 69481048, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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)+.

Workup

  1. additionpoured onto ice
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-66df6a8e46b44f488bc87ff28a45e84e
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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