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Hydrogen Bromide → HCID 68580915, Verbindung

HRID 644777
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 644777
C(O[CH:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([N:24]2[CH:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[N:26]=[N:25]2)[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C(OC(=O)C)(=O)C.[BrH:40]>ClCCl.CC(O)=O>[C:8]([O:7][C@@H:6]1[C@@H:11]([N:24]2[CH:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[N:26]=[N:25]2)[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:18][C@@H:5]1[Br:40])(=[O:10])[CH3:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 260Hydrogen BromideHCID 7918Acetic AnhydrideHCID 68578563HCID 68578563, Verbindung

Produkt 1

HCID 68580915HCID 68580915, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

1,2,4,6-Tetra-O-acetyl-3-deoxy-3-[4-(methoxycarbonyl)-1H-1,2,3-triazol-1-yl]-D-galactopyranose 23 (33 mg, 0.072 mmol) was dissolved in dichloromethane (1 ml) which had been dried over 4 Å molecular sieves. Acetic anhydride (14 l, 0.20 mmol) and HBr (0.2 ml of a 33% solution in AcOH) were added, and the mixture was stirred under N2 at room temperature. After 3 h 15 min, the reaction mixture was diluted with dichloromethane (30 ml) and poured into ice-water (30 ml). The organic phase was washed with NaHCO3 (30 ml of a saturated aqueous solution), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography to give 24 (16 mg, 46%), which was used immediately in the synthesis of 25.

Aufarbeitung

  1. customhad been dried over 4 Å molecular sieves
  2. washThe organic phase was washed with NaHCO3 (30 ml of a saturated aqueous solution)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dbaf5b04145b40d8973b06fb526c945c
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07700763B2

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