HCID 10903732, Verbindung → Lamivudine

HRID 342512

Reaktionsgleichung

Reaktionsgleichung von HRID 342512
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([C@H:8]2[O:12][C@@H:11]([CH2:13][O:14]C(=O)C3C=CC=CC=3)[S:10][CH2:9]2)[C:4](=[O:23])[N:3]=1>CO>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([C@H:8]2[O:12][C@@H:11]([CH2:13][OH:14])[S:10][CH2:9]2)[C:4](=[O:23])[N:3]=1

Komponenten

3

Edukt 1

HCID 10903732HCID 10903732, Verbindung2×

Produkt 1

HCID 60825LamivudineAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension of (cis)-4-amino-1-(2-benzoyloxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one (Intermediate 3) (8.19 g) and Amberlite IRA-400 (OH) resin (8.24 g) in methanol (250 ml) was stirred and heated to reflux for 11/4 h. Solids were removed by filtration then washed with methanol. The combined filtrates were evaporated. The residue was triturated with ethyl acetate (80 ml). The resulting white solid was collected by filtration to give the title product (5.09 g), 1H NMR (DMSO-d6) 3.04 (1H), 3.40 (1H), 3.73 (2H), 5.18 (1H), 5.29 (1H), 5.73 (1H), 6.21 (1H), 7.19 (2H), 7,81 (1H).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 11/4 h
  3. customSolids were removed by filtration
  4. washthen washed with methanol
  5. customThe combined filtrates were evaporated
  6. customThe residue was triturated with ethyl acetate (80 ml)
  7. filtrationThe resulting white solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-dfcad035ce1a425dbb61dbbca1cb6cce
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859021

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