Reaction #167508

ord-8e62f655aef24c7888f7141542002154

Reaction equation

O=C(CCBr)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
bromoethylmannose
[N-]=[N+]=[N-].[Na+]
sodium azide
[I-].[Na+]
sodium iodide
→
[N-]=[N+]=NCCC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
azidoethylmannose

Reactants

O=C(CCBr)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
bromoethylmannose
[N-]=[N+]=[N-].[Na+]
sodium azide
[I-].[Na+]
sodium iodide

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherA 5 L round bottom three-necked flask, equipped with a heating mantle, an overhead stirrer
  2. 2
    Temperaturethe solution warmed to 50 C
  3. 3
    Concentrationconcentrated to dryness on the rotovap
  4. 4
    FiltrationThe combined organic portions are filtered
  5. 5
    Otherevaporated to dryness

Procedure

A 5 L round bottom three-necked flask, equipped with a heating mantle, an overhead stirrer, and a thermometer, is charged with 150 gm bromoethylmannose (525 mmol). The oil is dissolved in 2 L water and treated with 68.3 gm sodium azide (1.05 mol, 2 equiv.; 65 gm/mol; Alfa-Aesar) followed by 7.9 gm sodium iodide (52.5 mmol, 0.08 equiv.; 149.89 gm/mol; Alfa-Aesar) and the solution warmed to 50 C and stirred overnight. The solution is cooled to room temperature and concentrated to dryness on the rotovap. The solid residue is digested with 3×500 mL of 5:1 vol. CHCl3:MeOH at 40 C. The combined organic portions are filtered and evaporated to dryness to afford azidoethylmannose as an off-white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08846103B2uspto-grants-2014_09