반응 #92133

ord-8a07bb9d7ef04c08b481c6eef36e45dc

반응 조건

온도
25°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타Into a 50-mL round bottom flask, was placed
  2. 2
    기타to react
  3. 3
    workup.STIRRINGwith stirring, for an additional 5 h at 25° C
  4. 4
    기타The reaction was then quenched by the addition of 10 ml of water
  5. 5
    추출The resulting solution was extracted with 2×10 ml of ethyl acetate
  6. 6
    세척The resulting mixture was washed with 3×10 mL of brine
  7. 7
    농축The resulting mixture was concentrated under vacuum
  8. 8
    기타This resulted in 50 mg (79%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]imidazolidin-4-one as yellow oil

실험 절차

Into a 50-mL round bottom flask, was placed 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)benzoic acid (50 mg, 0.10 mmol, 1.00 equiv), N,N-dimethylformamide (2 mL), EDCI (38 mg, 0.20 mmol, 2.00 equiv), HOBt (27 mg, 0.20 mmol, 2.02 equiv), TEA (50 mg, 0.49 mmol, 5.00 equiv), imidazolidin-4-one (17 mg, 0.20 mmol, 2.00 equiv). The resulting solution was stirred for 30 min at 25° C. The resulting solution was allowed to react, with stirring, for an additional 5 h at 25° C. The reaction was then quenched by the addition of 10 ml of water. The resulting solution was extracted with 2×10 ml of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×10 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a TLC plate with PE/EA (1/1). This resulted in 50 mg (79%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]imidazolidin-4-one as yellow oil.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09447084B2uspto-grants-2016_09