Potassium Hydroxide → HCID 58767558, compound

HRID 1710452Notes

Reaction equation

HRID 1710452 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]3[CH:17]=[C:18]4[C:25](=[O:26])[NH:24][CH2:23][CH:22]([CH3:27])[N:19]4[C:20]=3[CH:21]=2)=[O:12])=[CH:6][CH:5]=1.[OH-].[K+]>CCO>[CH3:27][CH:22]1[N:19]2[C:20]3[CH:21]=[C:13]([C:11]([NH:10][C:7]4[CH:6]=[CH:5][C:4]([C:3]([OH:28])=[O:2])=[CH:9][CH:8]=4)=[O:12])[CH:14]=[CH:15][C:16]=3[CH:17]=[C:18]2[C:25](=[O:26])[NH:24][CH2:23]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58767562HCID 58767562, compound

Product 1

HCID 58767558HCID 58767558, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 1b (Example 1) (33 mg, 0.09 mmol) in EtOH (2 mL) was added 10% of aqueous KOH (174 uL, 0.35 mmol). The mixture was heated to 80° C. for 3 h. The reaction was cooled to room temperature and concentrated. The resulting residue was dissolved in water (7 mL) and acidified with 6 N HCl to pH ˜2. A large amount of white precipitate formed which was filtered and rinsed with ether and dried in the vacuum oven (50° C.) to provide 18 mg of the title compound, yield 57%. ESI-MS m/z 362.37 [M−H]−.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in water (7 mL)
  4. customA large amount of white precipitate formed which
  5. filtrationwas filtered
  6. washrinsed with ether
  7. customdried in the vacuum oven (50° C.)

Sources & evidence

ORD record
ord-b3c621489689496f99ed5febfff587f6
Source dataset
uspto-grants-2010_09
Patent number
US07790712B2

Reaction notes

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