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

HRID 1677006노트

반응식

HRID 1677006 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-6f5756084cf748749c13999c97b4d903
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008295B2

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