Pyridine → pentafluorophenyl 5-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate

HRID 1019034ノート

反応式

HRID 1019034 の反応式
F[C:2](F)(F)[C:3]([O:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]([F:15])[C:7]=1[F:16])=[O:4].[N:19]1([CH2:24][CH:25]=[CH:26][C:27]2[CH:28]=[CH:29][C:30]([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[C:31]([CH:35]=2)[C:32]([OH:34])=[O:33])[CH:23]=[CH:22][N:21]=[CH:20]1.N1C=CC=CC=1>CN(C=O)C>[N:19]1([CH2:24]/[CH:25]=[CH:26]/[C:27]2[CH:35]=[CH:31][C:30]([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[C:2]([CH:28]=2)[C:3]([O:5][C:6]2[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]([F:15])[C:7]=2[F:16])=[O:4])[CH:23]=[CH:22][N:21]=[CH:20]1.[N:19]1([CH2:24]/[CH:25]=[CH:26]\[C:27]2[CH:28]=[CH:29][C:30]([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[C:31]([CH:35]=2)[C:32]([O:34][C:6]2[C:7]([F:16])=[C:8]([F:15])[C:9]([F:14])=[C:10]([F:13])[C:11]=2[F:12])=[O:33])[CH:23]=[CH:22][N:21]=[CH:20]1

参加物

6

反応物 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 545106535-[3-(Imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoic acid

生成物 2

HCID 18399494pentafluorophenyl 5-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoateHCID 86758617pentafluorophenyl 5-[(Z)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Pentafluorophenyl trifluoroacetate (1.47 ml; 8.6 mmol) was added to a solution of 5-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoic acid (2.5 g, 7.14 mmol) and pyridine (0.7 ml; 8.6 mmol) in DMF (7 ml). After stirring at ambient temperature overnight, the mixture was evaporated to dryness and the residue extracted with ethyl acetate, washed with saturated sodium hydrogen carbonate solution and saturated brine. After evaporation the reaction mixture was purified by flash chromatography, eluting with dichloromethane/ethanol (99/1) to give E isomer pentafluorophenyl 5-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate and Z isomer pentafluorophenyl 5-[(Z)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate. Yield: 68%

後処理

  1. customthe mixture was evaporated to dryness
  2. extractionthe residue extracted with ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate solution and saturated brine
  4. customAfter evaporation the reaction mixture
  5. customwas purified by flash chromatography
  6. washeluting with dichloromethane/ethanol (99/1)

出典と根拠

ORDレコード
ord-51e20c7c773e4b4c8d36a1aa8f7c16b1
出典データセット
uspto-grants-2002_11
特許番号
US06486156B1

反応ノート

読み込み中…