Adenine → 9-[2'-Hydroxy-3'-octadecyloxypropyl]-adenine

HRID 442698

Reaktionsgleichung

Reaktionsgleichung von HRID 442698
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[O:17]1[CH:19]([CH2:20][O: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][CH2:38][CH3:39])[CH2:18]1.C(Cl)(Cl)Cl.CO>CN(C)C=O>[OH:17][CH:19]([CH2:20][O: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][CH2:38][CH3:39])[CH2:18][N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10]

Komponenten

6

Edukt 4

HCID 190AdenineHCID 11430Potassium CarbonateHCID 61831Oxirane, 2-[(octadecyloxy)methyl]-HCID 21584188Chloroform methanol

Produkt 1

HCID 158583749-[2'-Hydroxy-3'-octadecyloxypropyl]-adenineAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of adenine (0.829 g, 6.10 mmol), anhydrous potassium carbonate (45 mg) and rac-1,2-epoxy-3-octadecyloxypropane (2.0 g, 6.13 mmol) in anhydrous dimethylformamide (10 mL) is stirred at 70°-75° C. for 20 hours under a nitrogen atmosphere. The reaction mixture is filtered directly without cooling, and the filtrate is concentrated in vacuo to afford a white residue. The residue is stirred with 95:5 (v/v) chloroform-methanol. The insoluble solid is filtered, purified by chromatography, and dried in vacuo to give 0.9 g (31.8%) of 9-[2'-hydroxy-3'-octadecyloxypropyl]-adenine (CPR 1148): Thin-layer Chromatography (TLC); 4×8 cm silica gel 60, 0.25 mm thickness, 10:2:0.2 (v/v/v) CHCl3 -CH3OH-30% aqueous ammonia (Rf value=0.65); mp 151°-152° C.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered directly
  2. temperaturewithout cooling
  3. concentrationthe filtrate is concentrated in vacuo
  4. customto afford a white residue
  5. filtrationThe insoluble solid is filtered
  6. custompurified by chromatography
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f75d512e95f644aeaf44df9dcefc0069
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891881

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