Water → HCID 9803221, compound

HRID 1451519Notes

Reaction equation

HRID 1451519 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]([CH:18]([CH3:25])[CH2:19][C:20]([O:22]CC)=[O:21])=[C:8]2[CH3:26])=[CH:4][CH:3]=1.[OH-].[K+].O>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]([CH:18]([CH3:25])[CH2:19][C:20]([OH:22])=[O:21])=[C:8]2[CH3:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 19974944HCID 19974944, compound

Product 1

HCID 9803221HCID 9803221, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of the ester from Step 4 (5.13 g, 11.5 mmol) in 50 mL of EtOH was added 8N KOH (5 mL, 40 mmol) and 5 mL water. The mixture was heated to 60° C. for 1 h, then cooled and concentrated. The residue was partitioned between 1M HCl and EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated. Crystallization from CH2Cl2/ hexanes gave 3.59 g of the title compound.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between 1M HCl and EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customCrystallization from CH2Cl2/ hexanes

Sources & evidence

ORD record
ord-c292fa0f060a4646adbdc52b51e13241
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

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