Water → 1-Methyl-3(carboethoxypropyl)-7-(pivaloyloxymethyl)xanthine

HRID 263099

Reaktionsgleichung

Reaktionsgleichung von HRID 263099
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH:8]=[N:7][C:6]=2[NH:5][C:3]1=[O:4].C(=O)([O-])[O-].[Na+].[Na+].I[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].O>CN(C=O)C.CCO.C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][O:14][C:15](=[O:20])[C:16]([CH3:17])([CH3:19])[CH3:18])[CH:8]=[N:7][C:6]=2[N:5]([CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:3]1=[O:4]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10890062Ethyl 4-iodobutanoateHCID 128798411-Methyl-7-(pivaloyloxymethyl)xanthine

Produkt 1

HCID 128798421-Methyl-3(carboethoxypropyl)-7-(pivaloyloxymethyl)xanthineAusbeute 123,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21889567Chloroform ethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-methyl-7-(pivaloyloxymethyl)xanthine (350 mg, 1.25 mmes) sodium carbonate (265 mg, 2.50 mmoles) and ethyl 4-iodobutyrate (384 μl, 2.50 mmole) in 5.8 ml dry DMF was stirred under nitrogen at room temperature for 18 hours. Water was added and the reaction mixture extracted with chloroform. After drying, the extracts were stripped to leave a yellow oil which goes to chromotographed on four thick silica gel plates with 10% EtOH/CHCl3. The band was scraped off and eluted with 100 ml of 25% EtOH/CHCl3 to yield 609 mg of the desired product as an oil.

Aufarbeitung

  1. extractionthe reaction mixture extracted with chloroform
  2. customAfter drying
  3. customto leave a yellow oil which
  4. washeluted with 100 ml of 25% EtOH/CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-6d48475f834d47b1a6bcd738463e1005
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04156081

Verknüpfte Notizen

Wird geladen…