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Tetrabutylammonium Fluoride → Methyl 4-[[2-(4-Hydroxy-1-Piperidyl)Quinoline-4-carbonyl]Amino]-3,5-dimethyl-benzoate

HRID 239980
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HRID 239980 반응식
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:24]=[C:23]([C:25]([NH:27][C:28]3[C:37]([CH3:38])=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][C:29]=3[CH3:39])=[O:26])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:24]=[C:23]([C:25]([NH:27][C:28]3[C:29]([CH3:39])=[CH:30][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:36][C:37]=3[CH3:38])=[O:26])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH2:13][CH2:14]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707364Methyl 4-(2-(4-((tert-butyldimethylsilyl)oxy)piperidin-1-yl)quinoline-4-carboxamido)-3,5-dimethylbenzoate

생성물 1

HCID 86707365Methyl 4-[[2-(4-Hydroxy-1-Piperidyl)Quinoline-4-carbonyl]Amino]-3,5-dimethyl-benzoate수율 78.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of methyl 4-(2-(4-((tert-butyldimethylsilyl)oxy)piperidin-1-yl)quinoline-4-carboxamido)-3,5-dimethylbenzoate (0.21 g, 0.00038 mol) in THF (4 ml) is added Bu4NF 1.0 M in THF (4.0 ml) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 14 hours, the reaction mixture is diluted with ice-water and extracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography (silica gel) over a gradient using 0-40% ethyl acetate in hexanes to afford the title compound as a light yellow solid (0.13 g, 78%). Mass spectrum (m/z): 434.2 (M+1).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue
  6. customThe residue is purified by flash chromatography (silica gel) over a gradient

출처 및 근거

ORD 기록
ord-e73293fdba2f4825a74fcb9b668d1c4d
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642768B2

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