2,2,2-Trichloroethyl chloroformate → HCID 11078748, compound

HRID 974141Notes

Reaction equation

HRID 974141 reaction equation
Cl.[OH:2][CH:3]1[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@H:4]1[NH2:5].C(=O)([O-])O.[Na+].[Cl:19][C:20]([Cl:27])([Cl:26])[CH2:21][O:22][C:23](Cl)=[O:24]>O>[Cl:19][C:20]([Cl:27])([Cl:26])[CH2:21][O:22][C:23]([NH:5][C@@H:4]1[C@@H:6]([OH:7])[C@H:8]([OH:9])[C@@H:10]([CH2:12][OH:13])[O:11][CH:3]1[OH:2])=[O:24]

Participants

5

Reactant 3

HCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

Product 1

HCID 11078748HCID 11078748, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  1. temperatureby cooling in an ice bath
  2. temperaturecooling for 2 hours
  3. filtrationThe precipitate was collected by filtration
  4. washwashed successively with water and diethyl ether
  5. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-7d3fa47c876d4711a09ec14702af3b7f
Source dataset
uspto-grants-1991_11
Patent number
US05066794

Reaction notes

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