Hydrochloric Acid → 5'-o-Tert-butyldimethylsilyl-5-iodouridine

HRID 1384042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384042
N1C=CN=C1.[I:6][C:7]1[C:8](=[O:23])[NH:9][C:10](=[O:22])[N:11]([CH:21]=1)[C@@H:12]1[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[C@H:13]1[OH:14].[C:24]([Si:28]([CH3:31])([CH3:30])Cl)([CH3:27])([CH3:26])[CH3:25].Cl>CN(C=O)C>[Si:28]([O:19][CH2:18][C@H:17]1[O:20][C@@H:12]([N:11]2[CH:21]=[C:7]([I:6])[C:8](=[O:23])[NH:9][C:10]2=[O:22])[C@H:13]([OH:14])[C@@H:15]1[OH:16])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:31])[CH3:30]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12681085-Iodouridine

Produkt 1

HCID 156734805'-o-Tert-butyldimethylsilyl-5-iodouridineAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Imidazole (216 mg) was added to a mixture of triol 3a (490 mg) and tert-butyldimethylchlorosilane (239 mg) in 1 mL of DMF cooled by an ice bath. The mixture was allowed to warm to room temperature. After 16 hours, the mixture was poured into 0.1 M HCl (25 mL) and extracted with ethyl acetate (3×50 mL), the aqueous phases were washed with water, dried over anhydrous MgSO4, and concentrated in vacuo. Purification by flash chromatography (7% MeOH/CH2Cl2) gave 460 mg of the product as a colorless solid: 1H NMR (DMSO-d6) δ 0.08-0.12 (m, 6), 0.90 (s, 9), 3.72 (dd, 1), 3.80 (dd, 1), 3.90 (bs, 2), 4.02-3.98 (m, 1), 5.76 (d, 1), 7.93 (s, 1), 11.74 (bs, 1).

Aufarbeitung

  1. temperaturecooled by an ice bath
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washthe aqueous phases were washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (7% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-9fc858ce41fb4b99aad25a68a93b1e56
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258360B1

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