Triphenylphosphine → 5'-Carbethoxymethylene-3'-amino-5',3'-dideoxythymidine

HRID 443003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 443003
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([CH:25]=[CH:26][C@H:27]1[O:31][C@@H:30]([N:32]2[CH:40]=[C:38]([CH3:39])[C:36](=[O:37])[NH:35][C:33]2=[O:34])[CH2:29][C@@H:28]1[N:41]=[N+]=[N-])([O:22][CH2:23][CH3:24])=[O:21]>C1COCC1.O.CO.C(OCC)(=O)C>[NH3:32].[C:20]([CH:25]=[CH:26][C@H:27]1[O:31][C@@H:30]([N:32]2[CH:40]=[C:38]([CH3:39])[C:36](=[O:37])[NH:35][C:33]2=[O:34])[CH2:29][C@@H:28]1[NH2:41])([O:22][CH2:23][CH3:24])=[O:21]

Komponenten

6

Edukt 2

HCID 11776TriphenylphosphineHCID 540692895'-Carbethoxymethylene-3'-azido-5',3'dideoxythymidine

Produkt 2

HCID 222AmmoniaHCID 537410095'-Carbethoxymethylene-3'-amino-5',3'-dideoxythymidineAusbeute 185,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21584119Ethylacetate methanolLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

Triphenylphosphine (786 mg; 3 mM) was added to a stirred solution of the ester of Example 7 (16; 700 mg: 2.09 mM) in THF/H2O (10 ml/l ml) and the reaction was monitored by gas evolution via an attached gas bubbler. The reaction was completed after 3 hours. The mixture was evaporated in vacuo and the crude oil was chromatographed over SiO2 (50 g), eluting with 5% saturated. ammonia in methanol/ethyl acetate to afford a 93% yield (600 mg) of the title compound. Rf =0.3 (5% saturated. NH3 /MeOH in EtOAc). FAB-MS: MH+=310.

Aufarbeitung

  1. customThe mixture was evaporated in vacuo
  2. customthe crude oil was chromatographed over SiO2 (50 g)
  3. washeluting with 5% saturated

Quellen und Nachweise

ORD-Eintrag
ord-98e4a766594a47cd8ea37c286abda4ec
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892024

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