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

HRID 585388

反応式

HRID 585388 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-343db198108d4e11847fb16b4582bcdf
出典データセット
uspto-grants-2005_08
特許番号
US06930104B2

関連ノート

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