Deoxyadenosine → 8-Bromo-2'-deoxyadenosine

HRID 500293

Reaktionsgleichung

Reaktionsgleichung von HRID 500293
[C@@H:1]1([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13]([NH2:14])[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[Br:19]Br.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>C([O-])(=O)C.[Na+]>[Br:19][C:10]1[N:9]([C:18]2[N:17]=[CH:16][N:15]=[C:13]([NH2:14])[C:12]=2[N:11]=1)[C@@H:1]1[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1

Komponenten

6

Edukt 4

HCID 13730DeoxyadenosineHCID 14798Sodium HydroxideHCID 24408BromineHCID 656671Sodium Pyrosulfite

Produkt 1

HCID 965478-Bromo-2'-deoxyadenosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 517045Sodium AcetateLösungsmittel

Versuchsvorschrift

2′-Deoxyadenosine (7 gm. 25.9 mmol) was dissolved in sodium acetate buffer (150, 1 M, pH5.0) by worming it to about 50 C, then was cooled dawn to 30 C, then 3 ml of bromine in 100 ml of the same buffer was added dropwise at RT for 15 min., to the reaction. After, 6 hrs the TLC on silica gel (20% MeOH in CH2Cl2) showed that all starting material was converted to a new product. The reaction was discolored by adding some sodium metabisulfite (Na2S2O5) while it was stirring, the color changed to a white solution, the pH of the reaction was neutralized by adding NaOH (1M solution). The reaction mixture was kept at 4° C. (refrigerator) for 16 hrs. Next day the solid material was filtered, washed with cold water, then acetone to give a solid yellow powder product (5.75 gm. 64%). The structure of this product was confirmed by H NMR and ES-MS.

Aufarbeitung

  1. temperaturewas cooled dawn to 30 C
  2. custom6 hrs
  3. customwas kept at 4° C.
  4. customfor 16 hrs
  5. filtrationNext day the solid material was filtered
  6. washwashed with cold water
  7. customacetone to give a solid yellow powder product (5.75 gm. 64%)

Quellen und Nachweise

ORD-Eintrag
ord-139d759e39ce42ffbc1e82e600865e5f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07771929B2

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