Hydrogen Bromide → HCID 53636013, compound

HRID 1706838Notes

Reaction equation

HRID 1706838 reaction equation
[N:1]([CH2:4][C@@H:5]([OH:12])[C@@H:6]([OH:11])[CH2:7][CH2:8][CH:9]=O)=[N+:2]=[N-:3].[BrH:13].[C:14]([O:17]C(=O)C)(=O)[CH3:15]>Cl(O)(=O)(=O)=O>[C:14]([O:11][C@@H:6]1[C@@H:5]([CH2:4][N:1]=[N+:2]=[N-:3])[O:12][CH:9]([Br:13])[CH2:8][CH2:7]1)(=[O:17])[CH3:15]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 7918Acetic AnhydrideHCID 86737057HCID 86737057, compound

Product 1

HCID 53636013HCID 53636013, compound

Reagents, catalysts & solvents 1

HCID 24247Perchloric AcidCatalyst

Procedure

6-Azido-2,3,6-trideoxy-D-erythro-hexose (1.73 g, 10 mmol) was acetylated in acetic anhydride (8 ml) with a few drops of 70% perchloric acid as catalyst. After 1 h at room temperature the solution was saturated with dry hydrogen bromide and the mixture was allowed to stand for 2 h. It was then poured into ice-water and extracted with ice-water, ice-cold saturated sodium bicarbonate solution and water. Finally the extracts were dried (Na2SO4) and concentrated to yield 4-O-acetyl-6-azido-2,3,6-trideoxy-D-erythro-hexopyranosyl bromide as a colourless syrup (2.2 g), which was used immediately for the next step.

Workup

  1. extractionextracted with ice-water, ice-cold saturated sodium bicarbonate solution and water
  2. dry with materialFinally the extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-69b1356b7d0b4e1ea301afa258992388
Source dataset
uspto-grants-1980_06
Patent number
US04208531

Reaction notes

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