1-Bromo-3-methylbutane → HCID 60098544, Verbindung

HRID 896849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896849
Br[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:7][O:8][C:9](=[O:25])[C@H:10]([CH2:19][C:20]1[N:24]=[CH:23][NH:22][CH:21]=1)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[C:15]([O:14][C:12]([NH:11][C@@H:10]([CH2:19][C:20]1[N:24]=[CH:23][N:22]([CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5])[CH:21]=1)[C:9]([O:8][CH3:7])=[O:25])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Komponenten

5

Edukt 3

HCID 78911-Bromo-3-methylbutaneHCID 10340Sodium CarbonateHCID 178501431HCID 178501431, Verbindung

Produkt 1

HCID 60098544HCID 60098544, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Bromo-3-methylbutane (4.44 ml, 37.2 mmol) was added to a mixture of Nα-Boc-L-histidine methyl ester (5.0 g, 18.6 mmol) and sodium carbonate (4.0 g, 37.2 mmol) in acetonitrile (80 ml), and the mixture was heated under reflux for 18 hours. The cooled mixture was concentrated under reduced pressure. The residue was suspended in water and the suspension was basified using sodium carbonate then extracted with ethyl acetate (3×30 ml). The combined organic extracts were dried (Na2SO4) and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using an elution gradient of hexane:ethyl acetate (100:0 to 5:95) to afford the title compound as a colourless oil, 2.8 g. 1H-NMR (CDCl3, 400 MHz) δ: 0.90 (d, 6H), 1.40 (s, 9H), 1.50 (m, 1H), 1.60 (m, 2H), 2.96-3.06 (m, 2H), 3.62 (s, 3H), 3.82 (t, 2H), 4.50 (m, 1H), 5.85 (m, 1H), 6.62 (s, 1H), 7.32 (s, 1H). LRMS: m/z (ES+) 340 [MH+]. [α]D=−2.3 (c=0.22, methanol).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe cooled mixture was concentrated under reduced pressure
  4. extractionthen extracted with ethyl acetate (3×30 ml)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe residual oil was purified by column chromatography on silica gel using an elution gradient of hexane:ethyl acetate (100:0 to 5:95)

Quellen und Nachweise

ORD-Eintrag
ord-5f2a60698ae148509a63b79cd8358af5
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919457B2

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