反应详情

温度

-78 °C

The following reaction was carried out in a Fischer-Porter tube. Dimethoxyethane (76 ml) and 3.2 ml of concentrated sulfuric acid were added in that order to 4.0 g of 4-amino-(2S)-hydroxybutyric acid (AHBA), and the mixture was then cooled to −78° C. Isobutylene (38 ml) was added thereto, and the tube was sealed, followed by stirring at room temperature for 96 hr. The tube was then slowly opened, and isobutylene was removed by distillation at room temperature. The reaction mixture was then added dropwise to 128 ml of ice water, and the mixture was washed twice with 250 ml of ether, was cooled to 0° C., and was then neutralized with a 6 N aqueous sodium hydroxide solution. Further, solid sodium chloride was added to prepare a saturated solution, and the mixture was extracted four times with 100 ml of chloroform. The chloroform layers were combined, and the combined chloroform layers were dried over anhydrous sodium sulfate and were then concentrated under the reduced pressure to give 250 mg of a yellow oil. The yellow oil was purified by column chromatography on silica gel (30 g, chloroform-methanol-concentrated aqueous ammonia=20:1:0.05→9:2:0.1) to give 37.9 mg of intermediate 3 and 161 mg of intermediate 4.

1. customThe following reaction
2. customthe tube was sealed
3. customisobutylene was removed by distillation at room temperature
4. additionThe reaction mixture was then added dropwise to 128 ml of ice water
5. washthe mixture was washed twice with 250 ml of ether
6. temperaturewas cooled to 0° C.
7. additionFurther, solid sodium chloride was added
8. customto prepare a saturated solution
9. extractionthe mixture was extracted four times with 100 ml of chloroform
10. dry with materialthe combined chloroform layers were dried over anhydrous sodium sulfate
11. concentrationwere then concentrated under the reduced pressure