Chlorosuccinimide → 2,2-Dimethylpropionic acid [8-chloro-1-(2,2-dimethyl-propionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl ester

HRID 1792080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792080
[CH3:1][C:2]([CH3:35])([CH3:34])[C:3]([O:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH:23]=[O:24])[CH:12]=[N:11][C:10]=2[N:9]([CH2:25][O:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[C:8]1=[O:33])=[O:4].[Cl:36]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Cl:36][C:12]1[N:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH:23]=[O:24])[C:14]2[C:15](=[O:16])[N:7]([CH2:6][O:5][C:3](=[O:4])[C:2]([CH3:35])([CH3:34])[CH3:1])[C:8](=[O:33])[N:9]([CH2:25][O:26][C:27](=[O:32])[C:28]([CH3:29])([CH3:31])[CH3:30])[C:10]=2[N:11]=1

Komponenten

5

Edukt 2

HCID 31398ChlorosuccinimideHCID 23536861[1-(2,2-Dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionate

Produkt 1

HCID 235368902,2-Dimethylpropionic acid [8-chloro-1-(2,2-dimethyl-propionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl esterAusbeute 74,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2,2-Dimethylpropionic acid [1-(2,2-dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl ester (2.50 g) and N-chlorosuccinimide (896 mg) were dissolved in N,N-dimethylformamide (25 ml), and the mixture was stirred at room temperature for 8 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give 2.0 g of the title compound from the elution fraction of hexane-ethyl acetate (2:1).

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4827b0d3f5684e7292dc522efb21c879
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074798B2

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