Acetone → (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetic acid

HRID 2207035Notes

Reaction equation

HRID 2207035 reaction equation
[Br:1][C:2]1[C:11]([C@H:12]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][OH:14])=[C:10]([CH3:20])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:21])=[N:7]2.CC(C)=[O:24]>O>[Br:1][C:2]1[C:11]([C@H:12]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:13]([OH:24])=[O:14])=[C:10]([CH3:20])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:21])=[N:7]2

Participants

4

Reactant 2

HCID 180AcetoneHCID 66631978(S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethanol

Product 1

HCID 66631643(S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethanol (38 g, 108 mmol) in acetone (500 mL) was added RuCl3.3H2O (2.83 g, 10.83 mmol) followed by NaIO4 (116 g, 540 mmol) in H2O (400 mL) at 0° C. The mixture was stirred at room temperature for 2 hours. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product. LCMS-ESI+: calc'd for C17H20BrNO3: 366.1 (M+H+); Found: 366.0 (M+H+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-dde726f7ea584a089b68ba63fb9c674b
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

Loading…