Tetrabutylammonium Fluoride → 5-(4-(n-Trifluoroacetyl-2-aminoethoxy)but-2-yn-1-yl)-2',3'dideoxyuridine

HRID 76960

Reaktionsgleichung

Reaktionsgleichung von HRID 76960
[Si](O[O:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[CH:23]=[C:22]([CH2:24][C:25]#[C:26][CH2:27][O:28][CH2:29][CH2:30][NH:31][C:32](=[O:37])[C:33]([F:36])([F:35])[F:34])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:35][C:33]([F:34])([F:36])[C:32]([NH:31][CH2:30][CH2:29][O:28][CH2:27][C:26]#[C:25][CH2:24][C:22]1[C:20](=[O:21])[NH:19][C:17](=[O:18])[N:16]([CH:23]=1)[C@@H:14]1[O:15][C@H:11]([CH2:10][OH:9])[CH2:12][CH2:13]1)=[O:37]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 873650905'-O-tert-butyldimethylsilyloxy-(5-(4-(N-trifluoroacetyl-2-aminoethoxy)but-2-yn-1-yl))-2',3'-dideoxyuridine

Produkt 1

HCID 600251125-(4-(n-Trifluoroacetyl-2-aminoethoxy)but-2-yn-1-yl)-2',3'dideoxyuridineAusbeute 43,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4 (90.0 mg, 0.17 mmol) in THF (5 mL) was added 1.0 M tetrabutylammonium fluoride (TBAF, 0.2 mL, 0.19 mmol), which was stirred at r.t. for 3 h. After evaporating solvent, the organic residue was purified by silica gel column chromatography with MeOH/CH2Cl2 to give the product 5 (30 mg, 0.074 mmol, 43%). 1H NMR (CDCl3, 300 MHz) δ 8.01 (t, 1H, H6, J=1.2 Hz), 6.08 (dd, 1H, H1′, J=3.6 and 6.6 Hz), 4.23 (t, 2H, CH2), 4.20-4.10 (m, 1H, H4′), 3.85 (dd, 1H, H5′, J=3.3 and 11.4 Hz), 3.75-3.63 (m, 3H, H5′, CH2), 3.50-3.45 (m, 2H, CH2), 3.30-3.25 (m, 2H, CH2), 2.47-2.34 (m, 1H, H2′), 2.15-1.80 (m, 3H, H2′, 2 H3′). 19F NMR (CDCl3, 282.2 MHz) δ −77.79 (s, CF3).

Aufarbeitung

  1. customAfter evaporating solvent
  2. customthe organic residue was purified by silica gel column chromatography with MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-c391d243baf54e3f99fbab5cffa41432
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835625B2

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