Ammonium trifluoroacetate → 3-Cyclopropyl-5-pyridin-3-yl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester

HRID 545341ノート

反応式

HRID 545341 の反応式
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([N:14]([CH:28]1[CH2:30][CH2:29]1)[C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=1)[C:6](=O)[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].FC(F)(F)C([O-])=O.[NH4+:39]>CCO>[CH2:1]([O:3][C:4]([C:5]1[N:14]([CH:28]2[CH2:30][CH2:29]2)[C:15]([C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:20][CH:21]=2)=[N:39][C:6]=1[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:31])[CH3:2]

参加物

4

反応物 2

HCID 2724268Ammonium trifluoroacetateHCID 671330912-[Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-3-pyridin-3-yl-propionic acid ethyl ester

生成物 1

HCID 671331703-Cyclopropyl-5-pyridin-3-yl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester収率 80%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
110 °C

実験手順

To 1.2 g (3 mmol) of 2-[cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-3-pyridin-3-yl-propionic acid ethyl ester in 10 ml of EtOH was added 1.4 g (11 mmol) of ammonium trifluoroacetate. The EtOH was evaporated and the residue heated to 110° C. for 4 h. The cooled residue was partitioned between saturated sodium hydrogen carbonate solution and CH2Cl2. The organic phase was dried with sodium sulfate and concentrated. Purification by flash column chromatography [n-heptane/EtOAc 3:7 to 1:1] afforded 0.9 g (80%) of the title compound as a colorless solid. MS: 418.2 (MH+).

後処理

  1. customThe EtOH was evaporated
  2. customThe cooled residue was partitioned between saturated sodium hydrogen carbonate solution and CH2Cl2
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated
  5. customPurification by flash column chromatography [n-heptane/EtOAc 3:7 to 1:1]

出典と根拠

ORDレコード
ord-b0a82083842f42729063092905c2c2fd
出典データセット
uspto-grants-2011_05
特許番号
US07935707B2

反応ノート

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