Acetic Acid → N2-isobutyryl-3'-O-(methylthiomethyl)-5'-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

HRID 446687

Reaktionsgleichung

Reaktionsgleichung von HRID 446687
[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:31])[C:10]2[N:11]=[CH:12][N:13]([C:29]=2[N:30]=1)[C@@H:14]1[O:28][C@H:18]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C@@H:16]([OH:17])[CH2:15]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].C(O)(=O)C.C(OC(=O)C)(=O)C.C([O-])([O-])=O.[K+].[K+].[CH3:49][S:50]([CH3:52])=O>>[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:31])[C:10]2[N:11]=[CH:12][N:13]([C:29]=2[N:30]=1)[C@@H:14]1[O:28][C@H:18]([CH2:19][O:20][Si:21]([C:24]([CH3:26])([CH3:25])[CH3:27])([CH3:23])[CH3:22])[C@@H:16]([O:17][CH2:49][S:50][CH3:52])[CH2:15]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Komponenten

6

Edukt 5

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 1359094375'-O-TBDMS-N2-ibu-dG

Produkt 1

HCID 136404885N2-isobutyryl-3'-O-(methylthiomethyl)-5'-O-(tert-butyldimethylsilyl)-2'-deoxyguanosineAusbeute 69 %

Versuchsvorschrift

5 g of N2-isobutyryl-5′-O-(tert-butyldimethylsilyl)-2′-deoxyguanosine (11.0 mmol) dissolved in 21 mL dry DMSO was treated with 10 mL acetic acid and 32 mL acetic anhydride, and stirred for 48 h at room temperature. The crude reaction mixture was then neutralized by adding a K2CO3 solution, and extracted with ethyl acetate (100×3 mL). The combined organic extract was then washed with saturated NaHCO3 solution, dried over Na2SO4 and concentrated under vacuum. Then reaction mixture was purified by a silica gel column chromatography resulting the product 11 as white powder (3.9 g, 69% yield; Rf=0.35, CH2Cl2:MeOH/20:1). HR-MS: Obs. m/z 512.2344 cald. for C22H38O5N5SiS 512.2363 [M+H]+. 1H-NMR (CDCl3): δH 12.0 (s, 1H), 8.95 (brs, 1H), 8.09 (s, 1H), 6.24 (t, J=6.8 Hz, 1H), 4.73 (m, 2H), 4.66 (m, 1H), 4.16 (m, 1H), 3.81 (m, 2H), 2.76 (m, 1H), 2.59 (m, 1H), 2.54 (m, 1H), 2.21 (s, 3H), 1.29 (m, 6H), 0.91 (s, 9H), and 0.10 (s, 6H) ppm.

Aufarbeitung

  1. customThe crude reaction mixture
  2. extractionextracted with ethyl acetate (100×3 mL)
  3. extractionThe combined organic extract
  4. washwas then washed with saturated NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThen reaction mixture
  8. customwas purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6e7c6b089f554ffb87910a6d02dbaef3
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481259B2

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