Trifluoroacetic acid → 2,2,2-Trifluoro-1-[3-(3-fluorophenyl)azetidin-1-yl]ethanone

HRID 927975노트

반응식

HRID 927975 반응식
C(N1CC[C@@H:5]([NH:8][C:9]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2S(NC2C(C(OC)=O)=C3C(C4CC4CO3)=CC=2)(=O)=O)=O)C1)C.[F:38][C:39]([F:44])([F:43])[C:40](O)=[O:41]>C(Cl)Cl>[F:38][C:39]([F:44])([F:43])[C:40]([N:8]1[CH2:5][CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([F:18])[CH:17]=2)[CH2:9]1)=[O:41]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86713316methyl (1aRS,7bSR)-5-{2-[((R)-1-ethylpyrrolidin-3-ylcarbamoyl)methyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2회

생성물 1

HCID 867133152,2,2-Trifluoro-1-[3-(3-fluorophenyl)azetidin-1-yl]ethanone

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl 3-(3-fluorophenyl)azetidine-1-carboxylate (Intermediate 92, 2.51 g) in trifluoroacetic acid (15 mL) and DCM (15 mL) was left to stand at room temperature for 30 minutes. The mixture was concentrated in vacuo and the residue was azeotroped with toluene. The residue was dissolved in DCM (15 mL) and pyridine (5 mL) and trifluoroacetic anhydride (3.15 g) was added. The mixture was left to stand at room temperature for 30 minutes, then washed with 1M hydrochloric acid and filtered through a phase separator. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20% to give 2,2,2-trifluoro-1-[3-(3-fluorophenyl)azetidin-1-yl]ethanone (2.31 g) as a light brown oil.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was azeotroped with toluene
  3. dissolutionThe residue was dissolved in DCM (15 mL)
  4. additionpyridine (5 mL) and trifluoroacetic anhydride (3.15 g) was added
  5. waitThe mixture was left
  6. waitto stand at room temperature for 30 minutes
  7. washwashed with 1M hydrochloric acid
  8. filtrationfiltered through a phase separator
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe residue was purified by chromatography on silica
  11. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20%

출처 및 근거

ORD 기록
ord-413a2d0fb0b14076af32858b0c880b3f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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