Reaktion #10170

Reaktionsgleichung

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

Ausbeute 45.0%

Lösungsmittel

N,N-dimethylformamide

Water

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe reaction mixture was extracted with ethyl acetate
2. 2
   WaschenThe combined organic extracts were washed with water and brine
3. 3
   Trocknendried (sodium sulfate)
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give the crude product
6. 6
   SonstigeThis was purified by silica gel chromatography

Vorschrift

(±)-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.

Quelle