Potassium Hydroxide → HCID 22148934, compound

HRID 1451524Notes

Reaction equation

HRID 1451524 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22]C)=[O:21])=[C:8]2[CH3:26])=[CH:4][CH:3]=1.[OH-].[K+]>CCO>[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([OH:22])=[O:21])=[C:8]2[CH3:26])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19974930HCID 19974930, compound

Product 1

HCID 22148934HCID 22148934, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a room temperature solution of the methyl ester from Step 2 (24 mg, 0.052 mmol) in 10 mL EtOH was added 1 mL of 4N KOH. The solution was heated to reflux for 22 h, then cooled and concentrated in vacuo. The residue was partitioned between 1M HCl and EtOAc. The organic layer was washed with brine, dried over Na2SO4 and evaporated to provide 23 mg of the title compound.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 22 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between 1M HCl and EtOAc
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-78d4d4068b4743cfba89ab60bbf46ed7
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

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