Ammonium Acetate → HCID 178506376、化合物

HRID 419705ノート

反応式

HRID 419705 の反応式
O=[C:2]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:30])([F:29])[F:28])[CH:21]=1)[CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)=O.C([O-])(=O)C.[NH4+:35]>C(O)(=O)C>[F:28][C:27]([F:30])([F:29])[O:26][C:22]1[CH:21]=[C:20]([C:2]2[N:35]=[C:5]([CH:7]3[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]3)[NH:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=1

参加物

4

反応物 2

HCID 517165Ammonium AcetateHCID 66650102Tert-butyl 4-(2-oxo-2-(3-(trifluoromethoxy)phenyl)ethylcarbamoyl)piperidine-1-carboxylate

生成物 1

HCID 178506376HCID 178506376、化合物収率 45.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Add tert-butyl 4-(2-oxo-2-(3-(trifluoromethoxy)phenyl)ethylcarbamoyl)-piperidine-1-carboxylate (1.50 g, 3.48 mmol) to a mixture of ammonium acetate (1.40 g, 18.1 mmol), and glacial acetic acid (10 mL) and heat at reflux for 15 h. Cool the mixture to room temperature and concentrated in vacuo. Dissolve the residue in ethyl acetate (50 mL) and adjust to pH 8 with saturated NaHCO3. Extract the aqueous layer with ethyl acetate (2×50 mL). Combine the organic layers, dry (Na2SO4), filter, and concentrate in vacuo. Purify the residue by silica gel chromatography (80 g, eluting with a gradient of 10% to 20% methanol/ethyl acetate, 1.5 L) to provide 4-(4-(3-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)piperidine (491 mg, 45%).

後処理

  1. temperatureheat
  2. temperatureat reflux for 15 h
  3. concentrationconcentrated in vacuo
  4. dissolutionDissolve the residue in ethyl acetate (50 mL)
  5. extractionExtract the aqueous layer with ethyl acetate (2×50 mL)
  6. dry with materialCombine the organic layers, dry (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify the residue by silica gel chromatography (80 g
  10. washeluting with a gradient of 10% to 20% methanol/ethyl acetate, 1.5 L)

出典と根拠

ORDレコード
ord-ec672467612543f5990e403f1f8aded9
出典データセット
uspto-grants-2012_01
特許番号
US08093383B2

反応ノート

読み込み中…