Ammonium trifluoroacetate → HCID 178468520, 화합물

HRID 545344노트

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HRID 545344 반응식
[CH2:1]([O:3][C:4](=[O:39])[CH:5]([N:22]([CH:36]1[CH2:38][CH2:37]1)[C:23](=O)[C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)[C:6]([C:8]1[CH:9]=[N:10][C:11]([O:14]CC2C=CC=CC=2)=[CH:12][CH:13]=1)=O)[CH3:2].FC(F)(F)C([O-])=O.[NH4+:47]>CCO>[CH2:1]([O:3][C:4]([C:5]1[N:22]([CH:36]2[CH2:38][CH2:37]2)[C:23]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=2)=[N:47][C:6]=1[C:8]1[CH:9]=[N:10][C:11]([OH:14])=[CH:12][CH:13]=1)=[O:39])[CH3:2]

참가 물질

4

반응물 2

HCID 2724268Ammonium trifluoroacetateHCID 671330303-(6-Benzyloxy-pyridin-3-yl)-2-[cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-propionic acid ethyl ester

생성물 1

HCID 178468520HCID 178468520, 화합물수율 70%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
110 °C

실험 절차

To 1.4 g (3 mmol) of 3-(6-benzyloxy-pyridin-3-yl)-2-[cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-propionic acid ethyl ester in 5 ml of EtOH was added 1.4 g (10 mmol) of ammonium trifluoroacetate. The EtOH was evaporated and the residue heated to 110° C. for 16 h. The cooled residue was partitioned between saturated sodium hydrogen carbonate solution and CH2Cl2. The organic phase was dried with sodium sulfate and concentrated. The crude reside was re-dissolved in 10 ml of EtOH, a generous spatula of 10% palladium on activated charcoal was added, and the mixture stirred under an atmosphere of hydrogen for 1 h. The mixture was then filtered over Hyflo and concentrated. Purification by flash column chromatography [MeOH/EtOAc 4:96 to 1:9] afforded 0.8 g (70%) of the title compound as a colorless solid. MS: 434.2 (MH+).

후처리

  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. dissolutionThe crude reside was re-dissolved in 10 ml of EtOH
  6. additiona generous spatula of 10% palladium on activated charcoal was added
  7. filtrationThe mixture was then filtered over Hyflo
  8. concentrationconcentrated
  9. customPurification by flash column chromatography [MeOH/EtOAc 4:96 to 1:9]

출처 및 근거

ORD 기록
ord-cdccb0f9c152460cbf2ef451354e1a15
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935707B2

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