Benzyl chloroformate → methyl 3-(benzyloxycarbonyl)-5-tert-butyl-1H-pyrrole-2-carboxylate

HRID 18926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18926
N[C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].[H-].[Na+].[C:17](Cl)(=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.C(OCC)(=O)C>[CH2:19]([O:18][C:17]([C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12])=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 18322367methyl 3-amino-5-(tert-butyl)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 68682038methyl 3-(benzyloxycarbonyl)-5-tert-butyl-1H-pyrrole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of the previously prepared methyl 3-amino-5-tert-butyl-1H-pyrrole-2-carboxylate (0.400 g, 2.0 mmol) and NaH (60% w/w, 0.760 g, 4.5 mmol) in THF (4 mL) was stirred at room temperature for 30 min. To the resulting mixture was added benzyl carbonochloridate drop wise and stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The crude product was recrystallized from dichloromethane:hexane to afford the desired methyl 3-(benzyloxycarbonyl)-5-tert-butyl-1H-pyrrole-2-carboxylate (0.560 g) as a white solid.

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. washwashed with saturated sodium bicarbonate solution
  3. customThe crude product was recrystallized from dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-15201a1c4ea34fa8bc1c4db79bf5c082
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741479B2

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