Dideoxycytidine → Diisopropylaminomethylene 2',3'-dideoxycytidine

HRID 729053

Reaktionsgleichung

Reaktionsgleichung von HRID 729053
[C@@H:1]1([N:8]2[CH:15]=[CH:14][C:12]([NH2:13])=[N:11][C:9]2=[O:10])[O:7][C@H:4]([CH2:5][OH:6])[CH2:3][CH2:2]1.CO[CH:18](OC)[N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH:20]([N:19]([CH:18]=[C:2]1[CH2:3][C@@H:4]([CH2:5][OH:6])[O:7][C@H:1]1[N:8]1[CH:15]=[CH:14][C:12]([NH2:13])=[N:11][C:9]1=[O:10])[CH:23]([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Komponenten

4

Edukt 2

HCID 24066DideoxycytidineHCID 13161384Diisopropylformamide Dimethylacetal (>90%)

Produkt 1

HCID 131717010Diisopropylaminomethylene 2',3'-dideoxycytidineAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a typical reaction--previously dried 2',3'-dideoxycytidine (153 mg, 0.724 mmoles) prepared by the literature procedures described above is treated with diisopropylformamide dimethylacetal (1.27 g, 7.24 mmoles) in anhydrous DMF (2 mL) under an argon atmosphere. The contents are stirred overnight and then the solvent and excess reagent are removed by rotary evaporation. The syrupy residue remaining is crystallized from ethanol-ether to give pale lemon-colored crystals (185 mg, 79%) of diisopropylaminomethylene 2',3'-dideoxycytidine.

Aufarbeitung

  1. customIn a typical reaction
  2. customthe solvent and excess reagent are removed by rotary evaporation
  3. customThe syrupy residue remaining is crystallized from ethanol-ether

Quellen und Nachweise

ORD-Eintrag
ord-fa786e27cfb34f2f97e82278b77890f2
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05051498

Verknüpfte Notizen

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