Sodium Hydroxide → HCID 17859407, compound

HRID 1372785Notes

Reaction equation

HRID 1372785 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:21]([CH2:23][CH2:24][O:25][C:26]3[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][CH:27]=3)[CH3:22])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:21]([CH2:23][CH2:24][O:25][C:26]3[CH:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[CH:34][CH:35]=3)[CH3:22])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 17858822HCID 17858822, compound

Product 1

HCID 17859407HCID 17859407, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(2-((2-(2-methylphenylamino)-6-benzoxazolyl)-N-methylacetamido)ethoxy)benzoate (206.9 mg, 0.44 mmol) was dissolved in THF (5 ml). To the resulting solution was added 0.25N NaOH (5 ml), and the resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture was added NaOH (500 mg), followed by heating under reflux for 3 hours. After cooling, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was diluted with a chloroform-methanol mixture (5:1, v/v). The solution was washed with 1N HCl, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform-methanol (20:1, v/v) eluate fractions, the title compound (101 mg, 51%) was obtained as a pale red solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. distillationthe reaction mixture was distilled under reduced pressure
  5. customto remove the solvent
  6. additionThe residue was diluted with a chloroform-methanol mixture (5:1
  7. washThe solution was washed with 1N HCl
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform-methanol (20:1

Sources & evidence

ORD record
ord-73104f87be46479a99c21a22dfe220a4
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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