Reacción #617648

Ecuación de reacción

D-threonine

NaHCO3

n-Octyl chloroformate

→

title compound

Rendimiento 27.0%

(2R,3S)-3-hydroxy-2-{[(octyloxy)carbonyl]amino}butanoic acid

Rendimiento 27.0%

Disolventes

water

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction vigorously stirred 18 h at rt
2. 2
   Lavadowashed twice with Et2O
3. 3
   ExtracciónThe aqueous phase was extracted with AcOEt
4. 4
   Secadothe collected organic phases were dried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvent removed under vacuum

Procedimiento

In a round bottom flask, NaHCO3 (9.74 g, 116 mmol) was suspended in THF (25 mL) and water (50 mL), then D-threonine (5.47 g, 46.0 mmol) and tetrabutylamonium bromide (0.547 g) were added. n-Octyl chloroformate (10 mL, 51.1 mmol) was added dropwise and the reaction vigorously stirred 18 h at rt. The mixture was then diluted with water, washed twice with Et2O and pH adjusted to 2 with 2M HCl solution. The aqueous phase was extracted with AcOEt, the collected organic phases were dried over Na2SO4, filtered and the solvent removed under vacuum to give the title compound (3.37 g, 27%) as pale yellow oil, which was used in the next step without further purification. Rf=0.26 (Cy/EtOAc 2:8+1% CH3COOH; detection: ninhydrin, bromocresol green). FTIR (cm−1): 3340 (br), 2928, 2856, 1724 (br), 1526, 1261, 1074.

Fuente