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Chlorotrimethylsilane → HCID 15009334, Verbindung

HRID 1494501
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1494501
[CH2:1]=[C:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[O:12].C[Si](Cl)(C)C.[C:23](Cl)(=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].O.N>N1C=CC=CC=1.O>[CH2:1]=[C:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14]([NH:15][C:23](=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:13][C:11]1=[O:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 66982Decanoyl chlorideHCID 30059132'-methyl-2'-deoxyidenecytidineHCID 12896473Azane;hydrate

Produkt 1

HCID 15009334HCID 15009334, VerbindungAusbeute 45,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 1049PyridineLösungsmittel

Versuchsvorschrift

2'-Deoxy-2'-methylidenecytidine, 239 mg, was dissolved in 5 ml of pyridine, and to the solution was added dropwise 0.63 ml of trimethylsilyl chloride under ice cooling. The mixture was stirred at room temperature for 5 minutes and then 0.83 ml of decanoyl chloride was added dropwise to the mixture under ice cooling, followed by stirring at room temperature for 2 hours. After the reaction, 2 ml of water was added to the reaction solution, stirring was conducted at room temperature for 5 minutes, and then 2 ml of concentrated ammonia water was added to the solution, followed by stirring for 15 minutes. After the reaction, the solution was partitioned with chloroform, and the chloroform layer was distilled off under reduced pressure. The residue was treated with a silica gel chromatography (elution solvent-chloroform: methanol=25:1) to give 179 mg of the objective compound as an oleaginous product. Yield: 45.6%

Aufarbeitung

  1. stirringby stirring at room temperature for 2 hours
  2. additionwas added to the reaction solution
  3. stirringstirring
  4. waitwas conducted at room temperature for 5 minutes
  5. stirringby stirring for 15 minutes
  6. customAfter the reaction
  7. customthe solution was partitioned with chloroform
  8. distillationthe chloroform layer was distilled off under reduced pressure
  9. additionThe residue was treated with a silica gel chromatography (elution solvent-chloroform: methanol=25:1)

Quellen und Nachweise

ORD-Eintrag
ord-209b11fcc276493abc54ec56062d5f24
Quelldatensatz
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05026835

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