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

HRID 545338노트

반응식

HRID 545338 반응식
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([N:9]([CH:23]1[CH2:25][CH2:24]1)[C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)[C:6](=O)[CH3:7])[CH3:2].FC(F)(F)C([O-])=O.[NH4+:34]>CO>[CH2:1]([O:3][C:4]([C:5]1[N:9]([CH:23]2[CH2:25][CH2:24]2)[C:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[N:34][C:6]=1[CH3:7])=[O:26])[CH3:2]

참가 물질

4

반응물 2

HCID 2724268Ammonium trifluoroacetateHCID 671333462-[Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-butyric acid ethyl ester

생성물 1

HCID 671330023-Cyclopropyl-5-methyl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester수율 73%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
110 °C

실험 절차

To 0.15 g (0.4 mmol) of 2-[cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-butyric acid ethyl ester in 5 ml of MeOH was added 0.2 g (1.5 mmol) of ammonium trifluoroacetate. The MeOH 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 0.1 g (73%) of the title compound as a colorless solid. MS: 355.2 (MH+).

후처리

  1. customThe MeOH 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]

출처 및 근거

ORD 기록
ord-bf1a936f3555424caba4336135c78e84
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935707B2

반응 노트

불러오는 중…