تفاعل #10170

معادلة التفاعل

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

المردود 45.0%

المذيبات

N,N-dimethylformamide

Water

triethylamine

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe reaction mixture was extracted with ethyl acetate
2. 2
   غسيلThe combined organic extracts were washed with water and brine
3. 3
   تجفيفdried (sodium sulfate)
4. 4
   تركيزconcentrated
5. 5
   أخرىto give the crude product
6. 6
   أخرىThis was purified by silica gel chromatography

الإجراء التجريبي

(±)-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.

المصدر