Реакция #10170

Уравнение реакции

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide

(±)-Trans-1-amino-3-oxabicyclo[3.1.0]hexan-2-one

3,3,3-trifluoropropionic acid

Hydroxybenzotriazole

→

3,3,3-trifluoro-N-[(±)-trans-2-oxo-3-oxabicyclo[3.1.0]hex-1-yl]-propanamide

Выход 45.0%

Растворители

N,N-dimethylformamide

Water

triethylamine

Условия реакции

Обработка

1. 1
   Экстракцияthe reaction mixture was extracted with ethyl acetate
2. 2
   ПромывкаThe combined organic extracts were washed with water and brine
3. 3
   Сушкаdried (sodium sulfate)
4. 4
   Концентрированиеconcentrated
5. 5
   Другоеto give the crude product
6. 6
   ДругоеThis was purified by silica gel chromatography

Методика

(±)-Trans-1-amino-3-oxabicyclo[3.1.0]hexan-2-one (128 mg, 1.13 mmol) was mixed with 3,3,3-trifluoropropionic acid in 2.3 mL of N,N-dimethylformamide. Hydroxybenzotriazole (17.4 mg, 0.11 mmol) was added followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (282 mg, 1.47 mmol). The pH of the reaction mixture was adjusted to 8.5 with triethylamine and the mixture was allowed to stir at ambient temperature for 2 hours. Water was then added and the reaction mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, then dried (sodium sulfate) and concentrated to give the crude product. This was purified by silica gel chromatography to afford 120 mg (45%) of 3,3,3-trifluoro-N-[(±)-trans-2-oxo-3-oxabicyclo[3.1.0]hex-1-yl]-propanamide.

Источник