Dicyclohexylcarbodiimide → 2-(6-Aminopurin-9-yl)ethoxymethyl-(3-hexadecoxypropoxy)phosphinic acid

HRID 10162

Reaktionsgleichung

Reaktionsgleichung von HRID 10162
[CH:1]1[N:6]=[C:5]2[N:7]([CH2:10][CH2:11][O:12][CH2:13][P:14]([OH:17])([OH:16])=[O:15])[CH:8]=[N:9][C:4]2=[C:3]([NH2:18])[N:2]=1.[CH2:19]([O:35][CH2:36][CH2:37][CH2:38]O)[CH2:20][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][CH3:34].C1CCC(N=C=NC2CCCCC2)CC1>N1C=CC=CC=1>[CH3:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:35][CH2:36][CH2:37][CH2:38][O:15][P:14]([OH:17])([CH2:13][O:12][CH2:11][CH2:10][N:7]1[C:5]2[N:6]=[CH:1][N:2]=[C:3]([NH2:18])[C:4]=2[N:9]=[CH:8]1)=[O:16]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 60172AdefovirHCID 1657533-(Hexadecyloxy)propan-1-ol

Produkt 1

HCID 4834712-(6-Aminopurin-9-yl)ethoxymethyl-(3-hexadecoxypropoxy)phosphinic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a mixture of adefovir (1.36 g, 5 mmol) and 3-hexadecyloxy-1-propanol (1.8 g, 6 mmol) in dry pyridine was added DCC (2.06 g, 10 mmol). The mixture was heated to reflux and stirred 18 h then cooled and filtered. The filtrate was concentrated under reduced pressure and the residue was applied to a short column of silica gel. Elution of the column with 9:1 dichloromethane/methanol yielded hexadecyloxypropyl-adefovir (HDP-ADV) as a white powder.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturethen cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washElution of the column with 9:1 dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-3ef1c6764a8d4e91a9de0d35ff77b2ac
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094772B2

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