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

HRID 927975ノート

反応式

HRID 927975 の反応式
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]

参加物

4

反応物 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-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-413a2d0fb0b14076af32858b0c880b3f
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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