Acetic Anhydride → (R)-1-(5-acetoxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine

HRID 1296396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1296396
[Cl:1][CH2:2][CH2:3][NH:4][C:5]1[NH:13][C:12]2[C:11](=[O:14])[N:10]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([OH:21])[CH3:20])[C:9](=[O:22])[N:8]([CH3:23])[C:7]=2[N:6]=1.C(N(CC)CC)C.[C:31](OC(=O)C)(=[O:33])[CH3:32]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:31]([O:21][C@H:19]([CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][N:10]1[C:11](=[O:14])[C:12]2[NH:13][C:5]([NH:4][CH2:3][CH2:2][Cl:1])=[N:6][C:7]=2[N:8]([CH3:23])[C:9]1=[O:22])(=[O:33])[CH3:32]

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69154242(R)-1-(5-hydroxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine

Produkt 1

HCID 69154552(R)-1-(5-acetoxyhexyl)-8-(2-chloroethylamino)-3-methylxanthineAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirring mixture of (R)-8-(2-chloroethylamino)-1-(5-hydroxyhexyl)-3-methylxanthine (2.2 g, 6.4 mmol), triethylamine (1.94 g, 19.2 mmol) and 4-dimethylaminopyridine (0.39 g, 3.2 mmol) in chloroform (50 ml) at 0-5° C. was added acetic anhydride (1.30 g, 12.8 mmol). The mixture was warmed to room temperature, stirred overnight, and concentrated under reduced pressure. The residue was purified by column chromatography eluting with ethylacetate-methanol (7:1) to provide (R)-1-(5-acetoxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine (2.2 g, 89% yield) as a white powder.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography
  3. washeluting with ethylacetate-methanol (7:1)

Quellen und Nachweise

ORD-Eintrag
ord-277c249a883c415d872db9d741c0a732
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07247630B2

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