1,1'-Carbonyldiimidazole → tert-butyl 2-oxo-2-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)ethylcarbamate

HRID 1864030

Reaktionsgleichung

Reaktionsgleichung von HRID 1864030
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]([NH:20][CH2:21][C:22]([OH:24])=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[C:25]1([CH:31]2[NH:36][CH2:35][CH2:34][N:33]3[CH:37]=[CH:38][CH:39]=[C:32]23)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[N-]1C=CN=C1.C(NCC(O)=O)(OC(C)(C)C)=O>ClCCCl>[O:24]=[C:22]([N:36]1[CH2:35][CH2:34][N:33]2[CH:37]=[CH:38][CH:39]=[C:32]2[CH:31]1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:21][NH:20][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]

Komponenten

6

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27709101-phenyl-1H,2H,3H,4H-pyrrolo(1,2-a)pyrazineHCID 86621298Boc-glycine imidazolide

Produkt 1

HCID 67401960tert-butyl 2-oxo-2-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)ethylcarbamateAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

(1.1 g, 7.0 mmol) of CDI were added to a solution of Boc-glycine (1.2 g, 6.7 mmol) in DCE (20 ml), and stirring was carried out for 100 min at RT. (1.3 g, 6.7 mmol) of 1-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine (A2) were then added, and stirring was carried out for a further 2 h at RT. The mixture was then heated for 2 h at 50° C. (450 mg, 2 mmol) of Boc-glycine imidazolide were subsequently added, and the mixture was heated for 2 h under reflux. After cooling to RT, washing was carried out with, in succession, a 5% aq. sodium carbonate solution, a 5% aq. citric acid solution, water and brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. CC (DCE) with the residue yielded 1.4 g (4.1 mmol, 61%) of tert-butyl 2-oxo-2-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)ethylcarbamate.

Aufarbeitung

  1. stirringstirring
  2. waitwas carried out for a further 2 h at RT
  3. additionwere subsequently added
  4. temperaturethe mixture was heated for 2 h
  5. temperatureunder reflux
  6. washwashing
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9968b7d6be844da4914308379ccdf687
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625900B2

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