Iodoethane → HCID 67160209, Verbindung

HRID 1951218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1951218
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[NH:14][N:13]=[N:12][N:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:18](I)[CH3:19]>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:11]=[N:12][N:13]([CH2:18][CH3:19])[N:14]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178453348HCID 178453348, Verbindung

Produkt 1

HCID 67160209HCID 67160209, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of [2-(1H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester (prepared by the protocols outlined in N. A. Delaney, G. C. Rovnyak and M. Loots, European Patent specification EP 449523) (1.0 g, 4.69 mmol) in dry THF (20 ml) is treated with a 60% dispersion of sodium hydride in mineral oil (0.19 g, 4.69 mmol) and stirred at ambient temperature for 10 minutes. Ethyliodide (0.375 ml, 4.69 mmol) is added and the reaction mixture is heated at reflux for 7 hours, then diluted with ethyl acetate and filtered. The filtrate is evaporated and the residue purified by flash silica chromatography (elution 3:2 hexane/ethyl acetate) to afford the titled compound, [2-(2-ethyl-2H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester, eluted first and [2-(1-ethyl-1H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester, eluted second.

Aufarbeitung

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 7 hours
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue purified by flash silica chromatography (elution 3:2 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-dee31644ec3248f19040b4d79eb6a64f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404684B2

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