Sodium Hydroxide → HCID 43566624, compound

HRID 2365360Notes

Reaction equation

HRID 2365360 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([O:19]C)=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59625812HCID 59625812, compound

Product 1

HCID 43566624HCID 43566624, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 60e (0.18 g, 0.666 mmol) in EtOH (10 mL) was added 1N aqueous NaOH (2.5 mL, 2.5 mmol). The mixture was stirred at room temperature for 4 d. The solvent was evaporated and 1N aqueous HCl was added, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product 60f was purified by preparative reverse phase chromatography. MS m/z (M+H+) 257.1.

Workup

  1. customThe solvent was evaporated
  2. addition1N aqueous HCl was added
  3. extractionfollowed by extraction with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product 60f was purified by preparative reverse phase chromatography

Sources & evidence

ORD record
ord-080bde84cbf84c66b0f0dec08a79d2f9
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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