Acetic Acid Mixture with Hydrobromic Acid → HCID 54522117, compound

HRID 2051671Notes

Reaction equation

HRID 2051671 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([NH:5][C@@H:6]1[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:14]([CH3:20])[O:13][C@H:8](OC(=O)C)[C@@H:7]1[O:21][C:22](=[O:24])[CH3:23])=[O:4].[BrH:27].C(O)(=O)C>C(Cl)(Cl)Cl>[F:1][C:2]([F:26])([F:25])[C:3]([NH:5][C@@H:6]1[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:14]([CH3:20])[O:13][C@H:8]([Br:27])[C@@H:7]1[O:21][C:22](=[O:24])[CH3:23])=[O:4]

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 54370080HCID 54370080, compound

Product 1

HCID 54522117HCID 54522117, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The residue obtained from the reaction mixture by evaporation in vacuo, which consists of 3-trifluoroacetamido-1,2,4-tri-O-acetyl-3,6-dideoxy-β-L-talopyranose, is dissolved in 20 ml. of a 30% hydrogen bromide-acetic acid solution. After being kept for 2 hours at room temperature, 200 ml. of chloroform is added to the reaction mixture and the chloroform solution is washed with ice and water, a cold saturated sodium hydrogen carbonate solution, and water. The solution is dried over anhydrous magnesium sulfate and evaporated under reduced pressure to heavy syrup. The syrup is crystallized by adding ether, and recrystallization from a mixture of chloroform-ether gives 16 g. (92% yield) of 3-trifluoroacetamido-2,4-di-O-acetyl-3,6-dideoxy-β-L-talopyranosyl bromide.

Workup

  1. customThe residue obtained from the reaction mixture by evaporation in vacuo, which
  2. dissolutionis dissolved in 20 ml
  3. washthe chloroform solution is washed with ice and water
  4. dry with materialThe solution is dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure to heavy syrup
  6. customThe syrup is crystallized
  7. additionby adding
  8. customether, and recrystallization
  9. additionfrom a mixture of chloroform-ether
  10. customgives 16 g

Sources & evidence

ORD record
ord-746a8c14852642b7aaf4d76d54a30841
Source dataset
uspto-grants-1980_01
Patent number
US04181795

Reaction notes

Loading…