反应详情

To a mixture of benzoic acid (R)-3-{4-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]-3-methanesulfonylphenyl}-2-oxooxazolidin-4-ylmethyl ester (938 mg) described in Preparation Example 24, methylboronic acid (359 mg), palladium (II) acetate (34 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (123 mg) and potassium fluoride (697 mg) was added tetrahydrofuran (9 mL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was dissolved in methanol (3 mL) and 1,4-dioxane (3 mL) and 1N aqueous sodium hydroxide solution (6 mL) were added, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (113 mg).

1. temperaturethe mixture was refluxed for 8 hr
2. temperatureAfter cooling
3. extractionthe mixture was extracted with chloroform
4. washThe organic layer was washed with saturated brine
5. customthe solvent was evaporated
6. dissolutionThe obtained residue was dissolved in methanol (3 mL)
7. addition1,4-dioxane (3 mL) and 1N aqueous sodium hydroxide solution (6 mL) were added
8. additionWater was added to the reaction mixture
9. extractionthe mixture was extracted with chloroform
10. washThe organic layer was washed with saturated brine
11. customthe solvent was evaporated
12. customThe residue was purified by column chromatography (chloroform:methanol)