反应详情

3-Amino-4-methylbenzoic acid (1.5 g) is dissolved in a solution of sodium hydrogen carbonate (1.68 g) in water (25 ml), and to the mixture is added dropwise a solution of 2-acetylthiomethyl-3-phenylpropionyl chloride (2.86 g) in tetrahydrofuran (8 ml) with vigorously stirring, and the mixture is stirred at room temperature for 3 hours. Tetrahydrofuran is distilled off at a low temperature under reduced pressure, and the residue is washed with diethyl ether and acidified with hydrochloric acid, and the resulting oily substance is extracted with ethyl acetate. The extract is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and then the solvent is distilled off under reduced pressure. The oily residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected, and acetonitrile is distilled off under reduced pressure, and the precipitated crystals are separated by filtration to give the title compound (1.93 g).

1. stirringthe mixture is stirred at room temperature for 3 hours
2. distillationTetrahydrofuran is distilled off at a low temperature under reduced pressure
3. washthe residue is washed with diethyl ether
4. extractionthe resulting oily substance is extracted with ethyl acetate
5. washThe extract is washed with saturated aqueous sodium chloride solution
6. dry with materialdried over anhydrous sodium sulfate
7. distillationthe solvent is distilled off under reduced pressure
8. customThe oily residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
9. additionThe fractions containing the desired compound
10. customare collected
11. distillationacetonitrile is distilled off under reduced pressure
12. customthe precipitated crystals are separated by filtration