Hydrochloric Acid → (R)-1-(5-hydroxyhexyl)-3,7-dimethyluric acid

HRID 1835700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835700
C([O:4][C@H:5]([CH3:32])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:20](=[O:21])[C:19]2[N:18]([CH3:22])[C:16](=[O:17])[N:15](COC(=O)C(C)(C)C)[C:14]=2[N:13]([CH3:31])[C:11]1=[O:12])(=O)C.C[O-].[Na+].Cl>CO>[OH:4][C@H:5]([CH3:32])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:20](=[O:21])[C:19]2[N:18]([CH3:22])[C:16](=[O:17])[NH:15][C:14]=2[N:13]([CH3:31])[C:11]1=[O:12]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 53725271(R)-1-(5-acetoxyhexyl)-9-pivaloyloxymethyl-3,7-dimethyluric acid

Produkt 1

HCID 11601789(R)-1-(5-hydroxyhexyl)-3,7-dimethyluric acidAusbeute 30,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirring solution of (R)-1-(5-acetoxyhexyl)-9-pivaloyloxymethyl-3,7-dimethyluric acid (0.10 g, 0.22 mmol) in methanol (5 ml) was added solid sodium methoxide (48 mg, 0.88 mmol) in one portion. After stirring at room temperature for 4 days, the mixture was treated with 5% aqueous hydrochloric acid solution (0.25 ml) and concentrated under a stream of nitrogen and mild heating. The residue was purified by preparative thin layer chromatography (250 micron silica gel plate) eluting with 7% methanol-dichloromethane to provide (R)-1-(5-hydroxyhexyl)-3,7-dimethyluric acid (20 mg, 30 % yield) as awhite solid.

Aufarbeitung

  1. concentrationconcentrated under a stream of nitrogen and mild heating
  2. customThe residue was purified by preparative thin layer chromatography (250 micron silica gel plate)
  3. washeluting with 7% methanol-dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-fda418cd3359494c88253a65b635e6a5
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774130B2

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