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Acetic Anhydride → 7-(2-Thienyl)-3-(2,3-di-O-acetyl-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

HRID 1662293
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1662293
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([C@@H:15]3[O:21][C@H:20]([CH2:22][O:23]C(C4C=CC=CC=4)(C4C=CC(OC)=CC=4)C4C=CC(OC)=CC=4)[C@@H:18]([OH:19])[C@H:16]3[OH:17])[CH:13]=[N:14][C:7]=12.[C:47](OC(=O)C)(=[O:49])[CH3:48].C([O-])(O)=O.[Na+].[C:59](OCC)(=[O:61])[CH3:60]>N1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([C@@H:15]3[O:21][C@H:20]([CH2:22][OH:23])[C@@H:18]([O:19][C:59](=[O:61])[CH3:60])[C@H:16]3[O:17][C:47](=[O:49])[CH3:48])[CH:13]=[N:14][C:7]=12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 674298087-(2-Thienyl)-3-[5-O-(4,4'-dimethoxytrityl)-beta-D-ribofuranosyl]-3H-imidazo[4,5-b]pyridine

Produkt 1

HCID 674282737-(2-Thienyl)-3-(2,3-di-O-acetyl-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

Compound 12 (120 mg, 0.19 mmol) was azeotroped three times with anhydrous pyridine. This was dissolved in anhydrous pyridine (1.9 ml), and 72 μl (0.76 mmol) of acetic anhydride was further added thereto. This mixture was stirred at room temperature for 7 hours and poured into 5% NaHCO3 (50 ml) and ethyl acetate (50 ml). The organic layer was washed once with saturated aqueous sodium chloride, dried over Na2SO4, and then evaporated under reduced pressure to remove the solvent. The residue was azeotroped twice with toluene and dissolved in CH2Cl2 (19 ml), followed by addition of 190 μl dichloroacetic acid at 0° C. This reaction mixture was stirred at 0° C. for 15 minutes. The mixture was poured into 5% NaHCO3 and extracted with CH2Cl2. The organic layer was washed once with saturated aqueous sodium chloride, dried over Na2SO4, and then evaporated under reduced pressure to remove the solvent. The product was purified by flash silica gel chromatography using a 2% methanol-methylene chloride solution as a solvent to give 77 mg of Compound 13 in a yield of 93%.

Aufarbeitung

  1. washThe organic layer was washed once with saturated aqueous sodium chloride
  2. dry with materialdried over Na2SO4
  3. customevaporated under reduced pressure
  4. customto remove the solvent
  5. customThe residue was azeotroped twice with toluene
  6. dissolutiondissolved in CH2Cl2 (19 ml)
  7. additionfollowed by addition of 190 μl dichloroacetic acid at 0° C
  8. stirringThis reaction mixture was stirred at 0° C. for 15 minutes
  9. additionThe mixture was poured into 5% NaHCO3
  10. extractionextracted with CH2Cl2
  11. washThe organic layer was washed once with saturated aqueous sodium chloride
  12. dry with materialdried over Na2SO4
  13. customevaporated under reduced pressure
  14. customto remove the solvent
  15. customThe product was purified by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e3fb6494cde74bc594ef5ac8a63fb765
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08030478B2

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