Benzoyl chloride → Octa-o-benzoyl-alpha-lactose

HRID 2261413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261413
[OH:1][C@H:2]1[O:21][C@H:20]([CH2:22][OH:23])[C@@H:7]([O:8][C@@H:9]2[O:17][C@H:16]([CH2:18][OH:19])[C@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[C:24]([O:1][C@H:2]1[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:7]([O:8][C@@H:9]2[O:17][C@H:16]([CH2:18][O:19][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:14]([O:15][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:13][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:10]2[O:11][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:5]([O:6][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:3]1[O:4][C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

4

Edukt 2

HCID 7412Benzoyl chlorideHCID 84571alpha-D-lactose

Produkt 1

HCID 16152476Octa-o-benzoyl-alpha-lactoseAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

α-Lactose (2.3 g, 6.38 mmol) was dissolved in 30 ml of anhydrous pyridine, benzoyl chloride (8.9 ml, 76.6 mmol) was added thereto at 0° C., and the mixture was stirred for 8 hrs at room temperature. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and successively washed with 1 N HCl, saturated NaHCO3 and brine. The extract was dried over MgSO4, concentrated under a reduced pressure, and purified by column chromatography (ethyl acetate:n-hexane=1:3), to obtain the title compound as a white solid (7.19 g).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washsuccessively washed with 1 N HCl, saturated NaHCO3 and brine
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated under a reduced pressure
  5. custompurified by column chromatography (ethyl acetate:n-hexane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-8684f960bab24e4a8b702b4a8fb5311f
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846975B2

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