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Piperidine → 4-[(1Z)-3-[(2S)-1-(tert-Butoxycarbonyl)pyrrolidinyl]-2-(ethoxycarbonyl)-3-oxo-1-propenyl]benzoic acid

HRID 458440
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HRID 458440 반응식
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])[CH3:2].N1CCCCC1.[C:27]([C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1)([OH:29])=[O:28]>C1C=CC=CC=1>[C:16]([O:15][C:13]([N:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[C:6](=[O:7])/[C:5](/[C:4]([O:3][CH2:1][CH3:2])=[O:20])=[CH:34]/[C:33]1[CH:36]=[CH:37][C:30]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]
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참가 물질

5

반응물 3

HCID 8082PiperidineHCID 120884-Formylbenzoic acidHCID 57407385(S)-1-Boc-2-(3-ethoxy-3-oxopropanoyl)pyrrolidine

생성물 1

HCID 695170454-[(1Z)-3-[(2S)-1-(tert-Butoxycarbonyl)pyrrolidinyl]-2-(ethoxycarbonyl)-3-oxo-1-propenyl]benzoic acid수율 76%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To a solution of tert-butyl (2S)-2-(3-ethoxy-3-oxopropanoyl)-1-pyrrolidinecarboxylate (5.0 g, 17.5 mmol) in benzene (50 ml) and piperidine (0.3 ml, 3 mmol) was added 4-carboxybenzaldehyde (2.63 g, 17.5 mmol), and the mixture was refluxed for 3 h. The cooled solution was washed with 0.1 N HCl twice. The aqueous layer was extracted three times with ether. The combined organic phases were dried (Na2SO4) and concentrated to give C as a tan solid (5.54 g, 76% yield). LCMS m/z 416 (M−H), 833 (2M−H).

후처리

  1. temperaturethe mixture was refluxed for 3 h
  2. washThe cooled solution was washed with 0.1 N HCl twice
  3. extractionThe aqueous layer was extracted three times with ether
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4bd65df298b643d681ea08624d373df6
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07189851B2

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