Methanol → HCID 10643625, Verbindung

HRID 1597064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1597064
[CH2:1]([Si:3]([C:8]#[C:9][C@:10]1([CH2:32][O:33]CC2C=CC=CC=2)[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C@H:12]([OH:23])[C@@H:11]1[O:24]CC1C=CC=CC=1)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].B(Cl)(Cl)Cl.N1C=CC=CC=1.CO>ClCCl>[CH2:1]([Si:3]([C:8]#[C:9][C@:10]1([CH2:32][OH:33])[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C@H:12]([OH:23])[C@@H:11]1[OH:24])([CH2:4][CH3:5])[CH2:6][CH3:7])[CH3:2]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 1049PyridineHCID 25135Boron TrichlorideHCID 107455044'-C-triethylsilylethynyl-3',5'-di-O-benzyluridine

Produkt 1

HCID 10643625HCID 10643625, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Compound 8 (1.50 g. 2.67 mmol) was dissolved in dichloromethane (75.0 ml), and a 1.0 M boron trichloride (26.7 ml, 26.7 mmol) in dichloromethane was added to the solution at −78° C. in an argon atmosphere, followed by stirring for three hours at the same temperature. A mixture of pyridine (10.0 ml) and methanol (20.0 ml) was added thereto at −78° C., followed by stirring for ten minutes. The reaction mixture was concentrated through distillation under reduced pressure, and the residue was partitioned with ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate and concentrated through distillation under reduced pressure. The residue was purified by means of silica gel column chromatography (silica gel 200 ml, eluent; chloroform:methanol=9:1), to thereby yield a white powdery compound (Compound 9; 0.95 g, 2.48 mmol, 92.9%).

Aufarbeitung

  1. additionwas added
  2. customat −78° C.
  3. stirringby stirring for ten minutes
  4. concentrationThe reaction mixture was concentrated through distillation under reduced pressure
  5. customthe residue was partitioned with ethyl acetate and water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated through distillation under reduced pressure
  8. customThe residue was purified by means of silica gel column chromatography (silica gel 200 ml, eluent; chloroform:methanol=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-d9979527f1934108a6447ceb2c51c7b0
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06291670B1

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