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

HRID 904272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 904272
[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)xanthine

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 ml 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-48aa61996d4241aeaec20ac03e45d158
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04230805

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