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Tributyltin Chloride → HCID 68159442, Verbindung

HRID 2360542
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2360542
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:10][CH:9]=[N:8][CH:7]=1.C([Li])CCC.C([Sn](Cl)(CCCC)CCCC)CCC.C1(C)C(C([O:38][C@@H:39]2[C@@H:43]([CH2:44][O:45]C(C3C(C)=CC=CC=3)=O)[O:42][C@@H:41]([N:55]3[C:59]4=[N:60][CH:61]=[CH:62][C:63](I)=[C:58]4[CH:57]=[CH:56]3)[CH2:40]2)=O)=CC=CC=1>C(OCC)C.CN(C=O)C>[C@@H:41]1([N:55]2[C:59]3=[N:60][CH:61]=[CH:62][C:63]([C:9]4[S:10][C:6]([C:2]5[S:1][CH:5]=[CH:4][CH:3]=5)=[CH:7][N:8]=4)=[C:58]3[CH:57]=[CH:56]2)[O:42][C@H:43]([CH2:44][OH:45])[C@@H:39]([OH:38])[CH2:40]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 15096Tributyltin ChlorideHCID 11217456Thiazole, 5-(2-thienyl)-HCID 131731282HCID 131731282, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 68159442HCID 68159442, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 5-(2-thienyl)thiazole (0.4 mmol) in diethyl ether was cooled to −78° C., and n-butyllithium (0.4 mmol, 1.57 M solution in hexane) was added thereto, followed by stirring at −78° C. for 30 min. Furthermore, tributylstannyl chloride was added thereto, followed by stirring at room temperature for 30 min. The reaction solution was separated between ethyl acetate and water. The organic layer was washed with saturated brine and concentrated, and 1-[2-deoxy-3,5-di-O-(toluoyl)-β-D-ribofuranosyl]-4-iodo-pyrrolo[2,3-b]pyridine (120 mg, 0.2 mmol), chlorobistriphenylphosphine palladium (5% mol), and DMF (2 mL) were added thereto, followed by stirring at 100° C. for 1 hr. The reaction solution was separated between ethyl acetate and water, and the organic layer was washed with saturated brine and water, dried over anhydrous sodium sulfate, and concentrated. After purification with a silica gel column and addition of sodium methoxide (1.6 mL), the resulting mixture was stirred at room temperature for 30 min. dDvas nucleoside (34 mg) was purified with a silica gel column and by HPLC.

Aufarbeitung

  1. stirringby stirring at room temperature for 30 min
  2. customThe reaction solution was separated between ethyl acetate and water
  3. washThe organic layer was washed with saturated brine
  4. concentrationconcentrated
  5. stirringby stirring at 100° C. for 1 hr
  6. customThe reaction solution was separated between ethyl acetate and water
  7. washthe organic layer was washed with saturated brine and water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customAfter purification
  11. additionwith a silica gel column and addition of sodium methoxide (1.6 mL)
  12. stirringthe resulting mixture was stirred at room temperature for 30 min. dDvas nucleoside (34 mg)
  13. customwas purified with a silica gel column and by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e9c2cd1ce0e3417bb6057d65505e55f5
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08686130B2

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