2,2,2-Trichloroethyl chloroformate → HCID 18647872, compound

HRID 1767161Notes

Reaction equation

HRID 1767161 reaction equation
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].Cl.[OH:11][CH:12]1[O:20][C@H:19]([CH2:21][OH:22])[C@@H:17]([OH:18])[C@H:15]([OH:16])[C@H:13]1[NH2:14].C([O-])(O)=O.[Na+]>O>[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5]([NH:14][C@H:13]([C@H:15]([C@@H:17]([C@@H:19]([CH2:21][OH:22])[OH:20])[OH:18])[OH:16])[CH:12]=[O:11])=[O:6]

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 18647872HCID 18647872, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,2,2-Trichloroethoxycarbonyl chloride (200 g, 0.944 mol) is added portionwise to a solution of D-glucosamine hydrochloride (v, 200 g, 0.927 mol) and NaHCO3 (200 g, 2.4 mol) in water (4 L) in a 10 L 3-neck round-bottom flask and the resulting mixture is mechanically stirred overnight at room temperature. The white precipitate that forms is collected by filtration using a 2 L fritted funnel washed with ether (2 L), and dried at high vacuum for 3 hours to give 297 g (90%) of 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucose as a white solid (MW 354.57).

Workup

  1. filtrationThe white precipitate that forms is collected by filtration
  2. washwashed with ether (2 L)
  3. customdried at high vacuum for 3 hours

Sources & evidence

ORD record
ord-3b46531812e04b978c6eeb8eaea25012
Source dataset
uspto-grants-2007_06
Patent number
US07232900B2

Reaction notes

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