Hydrogen Bromide → HCID 18666630, compound

HRID 355502Notes

Reaction equation

HRID 355502 reaction equation
C(O[CH:5]1[O:13][C@H:12]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[C@@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[Cl:19])(=O)C.[BrH:20]>ClCCl.C(O)(=O)C>[C:9]([O:8][C@@H:7]1[C@@H:12]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:13][CH:5]([Br:20])[C@@H:6]1[Cl:19])(=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 18666628HCID 18666628, compound

Product 1

HCID 18666630HCID 18666630, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

3,5-Di-O-acetyl-2-chloro-2-deoxy-α,β-D-ribofuranosyl acetate (the compound described by J. P. Schaumberg et al., in "J. Org. Chem.," 50, pp. 1651-1656, 1985) represented by the following formula (N) ##STR52## where Ac is acetyl group is dissolved in dichloromethane. To the resulting solution is added 30% hydrogen bromide in acetic acid to effect the reaction at room temperature overnight. The resulting reaction solution is concentrated and the remaining acetic acid is removed by azeotropic distillation with toluene, to yield 3,5-di-O-acetyl-2-chloro-2-deoxy-α,β-D-ribofuranosyl bromide [compound (O)] as a syrup.

Workup

  1. customthe reaction at room temperature overnight
  2. customThe resulting reaction solution
  3. concentrationis concentrated
  4. customthe remaining acetic acid is removed by azeotropic distillation with toluene

Sources & evidence

ORD record
ord-0e736969bd7348828c9f884ba416e5ce
Source dataset
uspto-grants-1998_11
Patent number
US05831072

Reaction notes

Loading…