反应详情

In 5 ml of DMF was suspended 360 mg (9.0 mmol) of 60% sodium hydride, and a solution of 0.92 ml (9.0 mmol) of thiophenol in 10 ml of DMF was added dropwise to the suspension under ice cooling. After stirring for 10 minutes, a solution of 1.38 g (3.0 mmol) of Compound 50 obtained in Example 41 in 10 ml of DMF was added thereto under ice cooling, followed by stirring at 100° C. for 10 hours. After the reaction mixture was cooled to room temperature, water was added thereto, and the mixture was extracted with chloroform. The aqueous layer was adjusted to pH 5 by addition of 4N hydrochloric acid and extracted with chloroform. The combined organic layer was washed with an aqueous solution of sodium chloride and dried. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1). The compound eluted as a component with low polarity was recrystallized from ether to give 302.8 mg (yield: 23%) of Compound 90 as white crystals. The substance eluted as a component with high polarity was recrystallized from ether/ethanol to give 787.9 mg (yield: 59%) of Compound 89 as white crystals.

1. stirringby stirring at 100° C. for 10 hours
2. extractionthe mixture was extracted with chloroform
3. additionThe aqueous layer was adjusted to pH 5 by addition of 4N hydrochloric acid
4. extractionextracted with chloroform
5. washThe combined organic layer was washed with an aqueous solution of sodium chloride
6. customdried
7. distillationThe solvent was distilled off
8. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1)
9. washThe compound eluted as a component with low polarity
10. customwas recrystallized from ether