Reaktion #569852

ord-3563ef59a36b44ba9e0cb0b1afeebd0a

Reaktionsgleichung

CC(C)O.Cc1ccccc1
toluene isopropanol
CCCCCCCCCCCCCCCCCCNC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
compound
CCCCCCCCCCCCCCCCCCNC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
N-Octadecyl-D-glucopyranosylamine
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CCCCCCCCCCCC(=O)Cl
dodecanoyl chloride
→
CCCCCCCCCCCCCCCCCCN(C(=O)CCCCCCCCCCC)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
N-Glucopyranosyl-N-octadecyldodecanamide

Edukte

CC(C)O.Cc1ccccc1
toluene isopropanol
CCCCCCCCCCCCCCCCCCNC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
compound
CCCCCCCCCCCCCCCCCCNC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
N-Octadecyl-D-glucopyranosylamine
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CCCCCCCCCCCC(=O)Cl
dodecanoyl chloride

Reagenzien

Keine

Lösungsmittel

C1CCOC1
tetrahydrofuran
C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe solid is filtered off
  2. 2
    Sonstigethe filtrate is evaporated in vacuo to a syrup
  3. 3
    Sonstigethe crude product is purified by column chromatography on silica gel 60 using 10:1 toluene/isopropanol as the mobile phase

Vorschrift

10 g of the compound from Example 1 are suspended in 20 ml of tetrahydrofuran, 10 g of sodium carbonate are added and 10 g of dodecanoyl chloride in 10 ml of tetrahydrofuran are then added dropwise. When the reaction is complete (checked by thin layer chromatography on silica gel 60 6:1 toluene/isopropanol), the solid is filtered off, the filtrate is evaporated in vacuo to a syrup, and the crude product is purified by column chromatography on silica gel 60 using 10:1 toluene/isopropanol as the mobile phase.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04574122uspto-grants-1986_03