Réaction #167170

Équation de réaction

water

MeI

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

NaH

→

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

Rendement 94.0%

Solvants

ethyl acetate

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONUpon completion of the addition
2. 2
   Autrethe solution was removed from the ice bath
3. 3
   Températureto warm to room temperature
4. 4
   Autrethe crude reaction mixture
5. 5
   workup.STIRRINGwith stirring
6. 6
   ConcentrationThe quenched mixture was concentrated in vacuo
7. 7
   Autrepartitioned between diethyl ether and water
8. 8
   ExtractionThe ether layer was extracted with sodium bicarbonate twice
9. 9
   Extractionextracted three times with ethyl acetate
10. 10
    LavageThe combined ethyl acetate layers were washed with water, sodium thiosulfate, water
11. 11
    Séchagedried with sodium sulfate
12. 12
    Concentrationconcentrated

Mode opératoire

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.

Source