반응 #10170

반응 방정식

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

수율 45.0%

용매

N,N-dimethylformamide

Water

triethylamine

반응 조건

후처리

1. 1
   추출the reaction mixture was extracted with ethyl acetate
2. 2
   세척The combined organic extracts were washed with water and brine
3. 3
   건조dried (sodium sulfate)
4. 4
   농축concentrated
5. 5
   기타to give the crude product
6. 6
   기타This was purified by silica gel chromatography

실험 절차

(±)-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.

출처