반응 #92136

반응 방정식

DIEA

4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)benzoic acid

imidazolidin-4-one

HATU

→

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

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타Into a 25-mL round-bottom flask, was placed
2. 2
   기타The reaction was then quenched by the addition of 10 mL of water
3. 3
   추출The resulting solution was extracted with 2×10 mL of ethyl acetate
4. 4
   세척The resulting mixture was washed with 3×10 mL of brine
5. 5
   농축The resulting mixture was concentrated under vacuum
6. 6
   기타This resulted in 100 mg (88%) 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 25-mL round-bottom flask, was placed a solution of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)benzoic acid (100 mg, 0.20 mmol, 1.00 equiv) in N,N-dimethylformamide (2 mL), imidazolidin-4-one (34 mg, 0.39 mmol, 2.00 equiv), HATU (150 mg, 0.39 mmol, 2.00 equiv), DIEA (51 mg, 0.39 mmol, 2.00 equiv). The resulting solution was stirred for 1 h at rt. 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 silica gel column with ethyl acetate/petroleum ether (1:0). This resulted in 100 mg (88%) 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