Sodium Hydroxide → HCID 17859407, compound

Participants

Reaction Steps

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.

Provenance & Evidence