N-bromobutanimide → HCID 89995466, Verbindung

HRID 1487296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487296
C1C(=O)N([Br:8])C(=O)C1.[C:9]([O:13][C:14]([NH:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:8][C:20]1[N:19]=[C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:17]([NH:16][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH:21]=1

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 89995465HCID 89995465, Verbindung

Produkt 1

HCID 89995466HCID 89995466, VerbindungAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of NBS (1.548 g, 8.70 mmol) in DMF (15 ml) was added slowly via addition funnel to a solution of ethyl 1-((tert-butoxycarbonyl)amino)-1H-imidazole-2-carboxylate (2.22 g, 8.70 mmol) in DMF (12 ml) at room temperature. The reaction was stirred at room temperature overnight. To the reaction was added a saturated solution of sodium bicarbonate until the yellow solution became a white suspension. The mixture was concentrated to dryness. The residue was partitioned between EtOAc and water. The organic phase was washed (brine), dried (Na2SO4) and concentrated to give a yellow viscous oil. The crude product was purified via silica gel column (Isco prep: 15-100% ethyl acetate/hexanes) to afford ethyl 4-bromo-1-((tert-butoxycarbonyl)amino)-1H-imidazole-2-carboxylate (1.52 g, 4.55 mmol, 52.3% yield) as a white solid. LCMS (Method B) m/z 334.1 [M+1], Br-pattern; 1H NMR (400 MHz, chloroform-d) δ 7.26 (s, 1H), 4.42 (q, J=7.1 Hz, 2H), 1.51 (s, 9H), 1.42 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. concentrationThe mixture was concentrated to dryness
  2. customThe residue was partitioned between EtOAc and water
  3. washThe organic phase was washed (brine)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a yellow viscous oil
  7. customThe crude product was purified via silica gel column (Isco prep: 15-100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-308cf20127e840e4baae57ab25485dcb
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428511B2

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