Реакция #617648

Уравнение реакции

D-threonine

NaHCO3

n-Octyl chloroformate

→

title compound

Выход 27.0%

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

Выход 27.0%

Растворители

water

water

THF

Условия реакции

Обработка

1. 1
   Другоеthe reaction vigorously stirred 18 h at rt
2. 2
   Промывкаwashed twice with Et2O
3. 3
   ЭкстракцияThe aqueous phase was extracted with AcOEt
4. 4
   Сушкаthe collected organic phases were dried over Na2SO4
5. 5
   Фильтрацияfiltered
6. 6
   Другоеthe solvent removed under vacuum

Методика

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.

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