반응 #339876

반응 방정식

aniline

N-Boc-trifluoromethionine

N-methylmorpholine

isobutyl chloroformate

→

product

수율 67.6%

Tert-Butyl (S)-1-(phenylcarbamoyl)-3-(trifluoromethylthio)propylcarbamate

수율 67.6%

용매

THF

N2

반응 조건

후처리

1. 1
   기타was adjusted to −78° C
2. 2
   workup.STIRRINGthe mixture was stirred for 2 minutes
3. 3
   여과the solid matters were filtered
4. 4
   workup.DISTILLATIONfollowed by distillation of THF under reduced pressure
5. 5
   기타The residue was purified by column chromatography (hexane/ethyl acetate=80/20

실험 절차

N-Boc-trifluoromethionine (200 mg, 0.659 mmol) was dissolved in 6.6 ml of dry THF in the presence of N2, and the temperature was adjusted to −78° C. Subsequently, N-methylmorpholine (0.09 ml, 0.794 mmol) was added thereto, and the mixture was stirred. Two minutes later, isobutyl chloroformate (0.10 ml, 0.794 mmol) was added thereto, and the mixture was stirred for 2 minutes. Finally, aniline (0.07 ml, 0.794 mmol) was added thereto. TLC was performed to confirm disappearance of the starting compound, and the solid matters were filtered, followed by distillation of THF under reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate=80/20 then 70/30), thereby the product (168.6 mg, 65%) was obtained.

출처