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

HRID 1677006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677006
[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]

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6f5756084cf748749c13999c97b4d903
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008295B2

Notizen zur Reaktion

Wird geladen…