Potassium Carbonate → 5-Fluoro-1-[2'-hydroxy-3'-octadecyloxypropyl]-cytosine

HRID 442700

Reaktionsgleichung

Reaktionsgleichung von HRID 442700
[F:1][C:2]1[C:3]([NH2:9])=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[O:16]1[CH:18]([CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:17]1>CN(C)C=O>[F:1][C:2]1[C:3]([NH2:9])=[N:4][C:5](=[O:8])[N:6]([CH2:17][CH:18]([OH:16])[CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 61831Oxirane, 2-[(octadecyloxy)methyl]-HCID 178509021HCID 178509021, Verbindung

Produkt 1

HCID 99556615-Fluoro-1-[2'-hydroxy-3'-octadecyloxypropyl]-cytosineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 5-fluorocytosine (0.80 g, 6.20 mmol), anhydrous potassium carbonate (40 mg) and anhydrous dimethyl formamide (15 mL) is heated to 70° C. under a nitrogen atmosphere. Then rac-1,2-epoxy-3-octadecyloxypropane (2.0 g, 6.13 mmol) is added to this mixture with stirring over a period of 1 hour. The resultant reaction mixture is stirred at 80°-90° C. (oil bath temperature) for 48 hours. The reaction mixture is cooled to room temperature and concentrated under reduced pressure (0.5 mm Hg) to afford the crude product as a cream solid. This crude material is purified by chromatography and dried in vacuo to give 0.6 g (22%) 5-fluoro-1-[2'-hydroxy-3'-octadecyloxypropyl]-cytosine (CPR 1152): Thin-layer Chromatography (TLC; 4×8 cm silica gel 60, 0.25 mm thickness): 8:2 (v/v) CHCl3 -CH3OH (Rf value=0.75); mp 118°-119° C.

Aufarbeitung

  1. customThe resultant reaction mixture
  2. stirringis stirred at 80°-90° C. (oil bath temperature) for 48 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. concentrationconcentrated under reduced pressure (0.5 mm Hg)
  5. customto afford the crude product as a cream solid
  6. customThis crude material is purified by chromatography
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7894995dc3184541915f2f5f6abd1e42
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891881

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