Pyridine → Ganciclovir Di-O-acetate

HRID 1194801

Reaktionsgleichung

Reaktionsgleichung von HRID 1194801
O.[OH:2][CH2:3][CH:4]([O:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:14](=[O:18])[NH:13][C:12]([NH2:19])=[N:11][C:10]1=2)[CH2:5][OH:6].[C:20](OC(=O)C)(=[O:22])[CH3:21].CN(C)[CH:29]=[O:30].N1C=CC=C[CH:33]=1>CCOCC>[C:20]([O:2][CH2:3][CH:4]([O:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:14](=[O:18])[NH:13][C:12]([NH2:19])=[N:11][C:10]1=2)[CH2:5][O:6][C:29](=[O:30])[CH3:33])(=[O:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 1360789939-[[2-Hydroxy-1-(hydroxymethyl)ethoxy]methyl]guanine hydrate

Produkt 1

HCID 135459822Ganciclovir Di-O-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 205 mg (0.75 mmole) of 9-(1,3-dihydroxy-2-propoxymethyl)guanine monohydrate, 1.5 ml of acetic anhydride, 6 ml of dry dimethylformamide, and 1.5 ml of dry pyridine was stirred at room temperature under a drying tube for 4 days. Then the mixture was diluted with 15 ml of Et2O. The solid was collected on a filter and washed with Et2O. After recrystallization from 2-methoxyethanol, yield of colorless crystals=149 mg (59% ), m.p. 239°-240°. The material was homogenous by TLC (9:1 CHCl3 ---MeOH), and NMR confirmed the assigned structure.

Aufarbeitung

  1. customThe solid was collected on
  2. filtrationa filter
  3. washwashed with Et2O
  4. customAfter recrystallization from 2-methoxyethanol, yield of colorless crystals=149 mg (59% ), m.p. 239°-240°

Quellen und Nachweise

ORD-Eintrag
ord-5e197afe03dd42ff8cb4487d27e480bd
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04816447

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