Citric Acid → ethyl 5-[({6-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}oxy)methyl]pyrazine-2-carboxylate

HRID 1879396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879396
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].Br[CH2:20][C:21]1[N:22]=[CH:23][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[C:14]([O:13][C:12]([NH:11][C:3]1[CH:4]=[C:5]2[C:9]([CH2:8][CH2:7][CH2:6]2)=[CH:10][C:2]=1[O:1][CH2:20][C:21]1[N:22]=[CH:23][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:25][CH:26]=1)=[O:18])([CH3:15])([CH3:17])[CH3:16]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 22050280Ethyl 5-(bromomethyl)pyrazine-2-carboxylateHCID 58398545tert-butyl N-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)carbamate

Produkt 1

HCID 58398420ethyl 5-[({6-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}oxy)methyl]pyrazine-2-carboxylateAusbeute 41,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1.00 g of tert-butyl (6-hydroxy-2,3-dihydro-1H-inden-5-yl)carbamate was dissolved in 10.0 mL of DMF, and 1.08 g of ethyl 5-(bromomethyl)pyrazine-2-carboxylate and 721 mg of potassium carbonate were added thereto, followed by stirring at 60° C. for 1 hour. The reaction liquid was poured into a 5% w/v aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with a 5% w/v aqueous citric acid solution, water, and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to obtain 690 mg of ethyl 5-[({6-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}oxy)methyl]pyrazine-2-carboxylate.

Aufarbeitung

  1. customThe reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a 5% w/v aqueous citric acid solution, water, and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-919b2524e9874eba8f6d6ccf6d787072
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314240B2

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