Hydrochloric Acid → HCID 22873065, Verbindung

HRID 1781573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1781573
[Br:1][C@@H:2]1[C@:6](C(=O)C)([OH:7])[C@@H:5]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[O:4][C@H:3]1[N:16]1[CH:23]=[C:22]([CH3:24])[C:20](=[O:21])[NH:19][C:17]1=[O:18].O.NN.Cl>O.C(#N)C>[Br:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[O:4][C@H:3]1[N:16]1[CH:23]=[C:22]([CH3:24])[C:20](=[O:21])[NH:19][C:17]1=[O:18]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 67581565HCID 67581565, Verbindung

Produkt 1

HCID 22873065HCID 22873065, VerbindungAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

400 ml of acetonitrile and 2.16 g (3 equivalents) of water were added to 16.2 g (40.0 mmol) of 2'-deoxy-2'-bromo-3',5'-O-diacetyl-5-methyluridine, and the mixture was stirred. The resulting solution was cooled to 0° C., 6.01 g (3 equivalents) of hydrazine monohydrate were added thereto, and the mixture was reacted for 20 hours at that temperature. 100 ml of water were added to the reaction mixture, which was then neutralized to a pH of 6.8 by adding 6 N-hydrochloric acid thereto. The acetonitrile layer was separated, washed with saturated saline solution, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 13.5 g of 2'-deoxy-2'-bromo-5'-O-acetyl-5-methyluridine. Its purity was 81.8%. Its yield was 76.0%.

Aufarbeitung

  1. customthe mixture was reacted for 20 hours at that temperature
  2. customThe acetonitrile layer was separated
  3. washwashed with saturated saline solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1599ec65fdd54d67a7b447137a9c1a30
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05633366

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