반응 #617648

반응 방정식

D-threonine

NaHCO3

n-Octyl chloroformate

→

title compound

수율 27.0%

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

수율 27.0%

용매

water

water

THF

반응 조건

후처리

1. 1
   기타the reaction vigorously stirred 18 h at rt
2. 2
   세척washed twice with Et2O
3. 3
   추출The aqueous phase was extracted with AcOEt
4. 4
   건조the collected organic phases were dried over Na2SO4
5. 5
   여과filtered
6. 6
   기타the solvent removed under vacuum

실험 절차

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.

출처