5'-Carbethoxymethylene-3'-azido-5',3'dideoxythymidine → 5'-Carbethoxymethyl-3'-amino-5',3'-dideoxythymidine

HRID 443002

Reaktionsgleichung

Reaktionsgleichung von HRID 443002
[C:1]([CH:6]=[CH:7][C@H:8]1[O:12][C@@H:11]([N:13]2[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]2=[O:15])[CH2:10][C@@H:9]1[N:22]=[N+]=[N-])([O:3][CH2:4][CH3:5])=[O:2]>CO.[Pd]>[C:1]([CH2:6][CH2:7][C@H:8]1[O:12][C@@H:11]([N:13]2[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]2=[O:15])[CH2:10][C@@H:9]1[NH2:22])([O:3][CH2:4][CH3:5])=[O:2]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 541086925'-Carbethoxymethyl-3'-amino-5',3'-dideoxythymidineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of the ester of Example 7 (16; 700 mg, 2.09 mM) in methanol (15 ml) was subjected to hydrogenation in a Parr apparatus (30 psi) in the presence of 10% Pd/C (210 mg; 30 wt %). The hydrogenation reaction was completed after 24 hours. The catalyst was filtered and the filtrate evaporated to give 620 mg (96%) of the title compound. Rf =0.3(5% saturated. NH3 in MeOH in EtOAc). FAB-MS: MH+=312.

Aufarbeitung

  1. customThe hydrogenation reaction
  2. filtrationThe catalyst was filtered
  3. customthe filtrate evaporated

Quellen und Nachweise

ORD-Eintrag
ord-27db14cd401e4464958bd137500af100
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892024

Verknüpfte Notizen

Wird geladen…