Реакция #167170

Уравнение реакции

water

MeI

2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid

NaH

→

2-tert-Butoxycarbonylamino-3-methoxy-3-methyl-butyric acid

Выход 94.0%

Растворители

ethyl acetate

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONUpon completion of the addition
2. 2
   Другоеthe solution was removed from the ice bath
3. 3
   Температураto warm to room temperature
4. 4
   Другоеthe crude reaction mixture
5. 5
   workup.STIRRINGwith stirring
6. 6
   КонцентрированиеThe quenched mixture was concentrated in vacuo
7. 7
   Другоеpartitioned between diethyl ether and water
8. 8
   ЭкстракцияThe ether layer was extracted with sodium bicarbonate twice
9. 9
   Экстракцияextracted three times with ethyl acetate
10. 10
    ПромывкаThe combined ethyl acetate layers were washed with water, sodium thiosulfate, water
11. 11
    Сушкаdried with sodium sulfate
12. 12
    Концентрированиеconcentrated

Методика

2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (1.0 g, 4.29 mmol) was dissolved in THF (14 mL) and cooled to 0° C. in an external ice/brine bath. MeI (2.13 mL, 34.3 mmol) was added at 0° C. Solid NaH (60% dispersion in mineral oil, 0.514 g, 12.87 mmol) was added slowly at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was diluted in ethyl acetate and water was added slowly with stirring. The quenched mixture was concentrated in vacuo and partitioned between diethyl ether and water. The ether layer was extracted with sodium bicarbonate twice. The combined bicarbonate layers were acidified with aqueous citric acid to pH 3 and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water, sodium thiosulfate, water, dried with sodium sulfate and concentrated to yield 2-tert-Butoxycarbonylamino-3-methoxy-3-methyl-butyric acid (0.99 g, 94%) as an oil.

Источник