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

HRID 1019055노트

반응식

HRID 1019055 반응식
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

참가 물질

6

반응물 3

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

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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 and saturated sodium chloride. 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%

후처리

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

출처 및 근거

ORD 기록
ord-ef4663cab2784bf281983517d7957d8b
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486156B1

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