Sodium ethoxide → HCID 10158702, compound

HRID 1866775Notes

Reaction equation

HRID 1866775 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2=[N:15][C:16](S(C)(=O)=O)=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])=[C:13]2[CH2:12][NH:11][C:10]1=[O:31].[CH3:32][CH2:33][O-:34].[Na+]>CCO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2=[N:15][C:16]([O:34][CH2:33][CH3:32])=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])=[C:13]2[CH2:12][NH:11][C:10]1=[O:31]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 10160942HCID 10160942, compound

Product 1

HCID 10158702HCID 10158702, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The product of Example 3 (0.0658 g, 0.147 mmol) was suspended in EtOH (2 mL) and stirred under argon. A 0.5 M solution of NaOEt in EtOH (0.587 mL, 0.294 mmol) was added. After 15 min the solvent was removed in vacuo, and the residue partitioned between EtOAc and H2O. The organic phase was washed with H2O (2×), satd aq NaCl (1×), dried over anhydrous Na2SO4, filtered, and evaporated to give the crude product. Flash chromatography on silica gel eluted with 0-5% EtOAc/CH2Cl2 gave the title compound as a white-amorphous solid. mp 191-194° C., LC MS m/z=415 (MH+) Rt=2.15 min.

Workup

  1. customAfter 15 min the solvent was removed in vacuo
  2. customthe residue partitioned between EtOAc and H2O
  3. washThe organic phase was washed with H2O (2×)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product
  8. washFlash chromatography on silica gel eluted with 0-5% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-fb77c274dda744a291bebc4faacff6d5
Source dataset
uspto-grants-2009_12
Patent number
US07629462B2

Reaction notes

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