1-Hydroxybenzotriazole → Ethyl 3-[[5-[4-(9H-9-carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoyl]amino]propionate

HRID 585388노트

반응식

HRID 585388 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)=[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.Cl.[CH2:44]([O:46][C:47](=[O:51])[CH2:48][CH2:49][NH2:50])[CH3:45].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[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]([NH:50][CH2:49][CH2:48][C:47]([O:46][CH2:44][CH3:45])=[O:51])=[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

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 223392535-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoic acid

생성물 1

HCID 22339326Ethyl 3-[[5-[4-(9H-9-carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoyl]amino]propionate수율 81.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]-pentanoic acid (0.50 g, 0.89 mmol) prepared in Example 128 was mixed with β-alanine ethyl ester hydrochloride (0.15 g, 1 mmol), N,N-dimethylformamide (10 ml), 1-hydroxybenzotriazole (0.14 g, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) (0.19 g, 1 mmol), followed by stirring overnight at room temperature. After distilling off the solvent, the residue was partitioned between ethyl acetate and saturated brine, washed 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=1/7) to give the titled compound (0.48 g, yield: 81%) as a white powder (cis:trans=3:1).

후처리

  1. distillationAfter distilling off the solvent
  2. customthe residue was partitioned between ethyl acetate and saturated brine
  3. washwashed
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent

출처 및 근거

ORD 기록
ord-343db198108d4e11847fb16b4582bcdf
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930104B2

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