Ethyl 5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoate → 5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoic acid

HRID 585385

반응식

HRID 585385 반응식
[CH:1]1[C:13]2[N:12]([CH:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([C:24](=[O:35])[C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=4)[CH:16]([CH2:36][CH2:37][CH2:38][CH2:39][C:40]([O:42]CC)=[O:41])[CH2:15]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>O1CCCC1.[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1[C:13]2[N:12]([CH:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([C:24](=[O:35])[C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=4)[CH:16]([CH2:36][CH2:37][CH2:38][CH2:39][C:40]([OH:42])=[O:41])[CH2:15]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 1

HCID 22339243Ethyl 5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoate

생성물 1

HCID 223392535-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoic acid수율 74%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

실험 절차

Ethyl 5-[4-(9H-9-carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoate (0.20 g, 0.34 mmol) prepared in Example 127 was dissolved in tetrahydrofuran (10 ml), to which 1N NaOH (5 ml) and tetrabutylammonium bromide (0.11 g, 0.34 mmol) were then added and stirred at room temperature for 4 hours and then at 60° C. for 4 hours. After the reaction mixture was partitioned between ethyl acetate and 1N HCl, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/5) to give the titled compound (0.14 g, yield: 74%) as a white crystal (cis:trans=4:1).

후처리

  1. additionwere then added
  2. waitat 60° C. for 4 hours
  3. customAfter the reaction mixture was partitioned between ethyl acetate and 1N HCl
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent

출처 및 근거

ORD 기록
ord-9eca8aaea73f4da58b6a33d96b03e621
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930104B2

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