N,N-Diethylethanamine trihydrofluoride → 3'-Deoxy-3'-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine

HRID 448664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448664
[Si]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@H:22]([O:34][CH2:35][CH2:36][O:37][CH3:38])[C@@H:21]1[CH2:39][I:40])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.F.F.F.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[I:40][CH2:39][C@@H:21]1[C@@H:20]([CH2:19][OH:18])[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@@H:22]1[O:34][CH2:35][CH2:36][O:37][CH3:38]

Komponenten

5

Edukt 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 235183415'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine

Produkt 1

HCID 235183313'-Deoxy-3'-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridineAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 5′-O-(tert-butyldiphenylsilyl)-3′-deoxy-3′-(iodomethyl)-2′-O-(2-methoxyethyl)-5-methyluridine (1.12 g, 1.65 mmol) and triethylamine trihydrofluoride (1.1 mL, 1.1 g, 6.7 mmol) in 20 mL of THF was stirred at rt for 24 h. The reaction mixture was diluted with 50 mL of ethyl acetate and washed with water and brine. The organic phase was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on a silica gel column. Gradient elution with 2:1, 1:2 and then 1:3 hexanes-EtOAc provided 504 mg of the title compound as a white foam.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on a silica gel column
  5. washGradient elution with 2:1, 1:2

Quellen und Nachweise

ORD-Eintrag
ord-f44eef38b87a4499a5e436f71d730ea8
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481712B2

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