Reaktion #1061323

ord-7d3fa47c876d4711a09ec14702af3b7f

Reaktionsgleichung

Cl.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
D-glucosamine hydrochloride
O=C([O-])O.[Na+]
sodium hydrogen carbonate
O=C(Cl)OCC(Cl)(Cl)Cl
trichloroethoxycarbonyl chloride
→
O=C(N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O)OCC(Cl)(Cl)Cl
N-trichloroethoxycarbonyl-D-glucosamine

Edukte

Cl.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
D-glucosamine hydrochloride
O=C([O-])O.[Na+]
sodium hydrogen carbonate
O=C(Cl)OCC(Cl)(Cl)Cl
trichloroethoxycarbonyl chloride

Reagenzien

Keine

Lösungsmittel

O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturby cooling in an ice bath
  2. 2
    Temperaturcooling for 2 hours
  3. 3
    FiltrationThe precipitate was collected by filtration
  4. 4
    Waschenwashed successively with water and diethyl ether
  5. 5
    Sonstigerecrystallized from 95% ethanol

Vorschrift

Thirty grams of D-glucosamine hydrochloride was dissolved in 500 ml of water, and 30.0 g of sodium hydrogen carbonate was added thereto, followed by cooling in an ice bath. To the cooled solution was added 27.5 ml of trichloroethoxycarbonyl chloride, and the mixture was stirred under ice-cooling for 2 hours and then at room temperature for 11 hours. The precipitate was collected by filtration, washed successively with water and diethyl ether, and recrystallized from 95% ethanol to obtain 42.3 g of N-trichloroethoxycarbonyl-D-glucosamine (Compound A) having a melting point of 183° to 184° C. (with decomposition).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05066794uspto-grants-1991_11