tert-Butyl (3-aminopropyl)carbamate → Ethyl 5-bromo-3-[({3-[(tert-butoxycarbonyl)amino]propyl}amino)sulfonyl]-1-(phenylsulfonyl)-1H-indole-2-carboxylate

HRID 1677006ノート

反応式

HRID 1677006 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:5]2[S:25](Cl)(=[O:27])=[O:26].[NH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37]>ClCCl.C(N(CC)CC)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:5]2[S:25]([NH:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:40])(=[O:27])=[O:26]

参加物

6

反応物 2

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

生成物 1

HCID 67371797Ethyl 5-bromo-3-[({3-[(tert-butoxycarbonyl)amino]propyl}amino)sulfonyl]-1-(phenylsulfonyl)-1H-indole-2-carboxylate

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 200 mg ethyl 5-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate (Example 3, Step A) in 2 mL dichloromethane, triethylamine was added (165 μL), followed by tert-butyl 3-aminopropylcarbamate (76 mg). The reaction was stirred for 2 hours at room temperature. The reaction was diluted with EtOAc, washed with saturated NaHCO3 and brine and dried over Na2SO4. The crude product was purified by flash chromatography on silica using EtOAc:hexane (1:3) as mobile phase to give the titled compound. ESI+ MS: 644 [M+H]+.

後処理

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. customThe crude product was purified by flash chromatography on silica

出典と根拠

ORDレコード
ord-6f5756084cf748749c13999c97b4d903
出典データセット
uspto-grants-2011_08
特許番号
US08008295B2

反応ノート

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