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Acetone → HCID 67582894, Verbindung

HRID 1416469
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1416469
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][C@H]3C[C@@H](O)C=C3)[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:38]CC1.C[C:43]([CH3:45])=[O:44].[C:46]([OH:50])([CH3:49])([CH3:48])C>O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][C@H:45]3[CH2:49][C@@H:46]([OH:50])[C@H:48]([OH:38])[C@@H:43]3[OH:44])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 67582038HCID 67582038, Verbindung

Produkt 1

HCID 67582894HCID 67582894, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318
Osmium Tetroxide
Katalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1S,4R)-(4-hydroxycyclopent-2-en-1-yl)oxy]quinazoline (1.30 g), a solution of osmium tetroxide in t-butanol (osmium tetroxide 252 mg/t-butanol 18.1 g) (532 mg) and 4-methylmorpholine N-oxide (375 mg) in water (3 ml)--acetone (25 ml) is stirred at room temperature for 17 hours. Acetone is distilled off from the reaction mixture under reduced pressure, and to the resultant is added ethyl acetate, and the mixture is washed with 10% aqueous sodium sulfite solution and water. The ethyl acetate solution is dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure, and the residue is purified by medium pressure liquid column chromatography (eluent, chloroform:methanol=50:1, 10:1, v/v) to give 2-[4-(benzyloxycarbonyl) piperazin-1-yl]-4-[(1S,2S,3S,4R)-(2,3,4-trihydroxycyclopentan-1-yl)oxy]quinazoline (1.05 mg) as foam.

Aufarbeitung

  1. distillationAcetone is distilled off from the reaction mixture under reduced pressure
  2. additionto the resultant is added ethyl acetate
  3. washthe mixture is washed with 10% aqueous sodium sulfite solution and water
  4. dry with materialThe ethyl acetate solution is dried over anhydrous magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customthe residue is purified by medium pressure liquid column chromatography (eluent, chloroform

Quellen und Nachweise

ORD-Eintrag
ord-406e7175fe7640168833f420db5495f4
Quelldatensatz
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05912247

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