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Aluminium lithium hydride → 2,6-dichloro-N-[(1R)-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]-1-(hydroxymethyl)ethyl]benzamide

HRID 1869815
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HRID 1869815 반응식
[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:3]=1[C:4]([NH:6][C@H:7]([CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30])[CH:17]=[CH:16]2)[C:8](OC)=[O:9])=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:3]=1[C:4]([NH:6][C@@H:7]([CH2:8][OH:9])[CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30])[CH:17]=[CH:16]2)=[O:5]
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참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 86619055methyl (2R)-2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate

생성물 1

HCID 685938592,6-dichloro-N-[(1R)-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]-1-(hydroxymethyl)ethyl]benzamide수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To methyl (2R)-2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 36 (0,222 g) in THF (1 ml) is added, at 0° C., LiAlH4 (1.5 equ.). The solution is stirred at 0° C. for 1 hour. The reaction is quenched at −25° C. by successive additions of water (25 μl), 15% NaOH (25 μl) and water (75 μl). After evaporation of THF under vacuum, AcOEt is added. The organic phases are washed with water, brine, dried over MgSO4 and evaporated. The resulting residue is purified over silica gel using CH2Cl2/CH3OH/NH4OH (99/1/0.1) as eluent to give 2,6-dichloro-N-[(1R)-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]-1-(hydroxymethyl)ethyl]benzamide 60.

후처리

  1. customThe reaction is quenched at −25° C. by successive additions of water (25 μl), 15% NaOH (25 μl) and water (75 μl)
  2. customAfter evaporation of THF under vacuum, AcOEt
  3. additionis added
  4. washThe organic phases are washed with water, brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe resulting residue is purified over silica gel

출처 및 근거

ORD 기록
ord-1c00855592314e91bf7f2012ac816d12
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07638630B2

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