Sodium Hydroxide → HCID 58907068, compound

HRID 1295102Notes

Reaction equation

HRID 1295102 reaction equation
C([O:3][C:4](=[O:42])[C:5]([CH3:41])([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:24]2[S:28][C:27]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)=[N:26][C:25]=2[CH3:39])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])=[CH:10][C:9]=1[CH3:40])[CH3:6])C.[OH-].[Na+]>CCO>[CH3:41][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:24]2[S:28][C:27]([C:29]3[CH:30]=[CH:31][C:32]([C:35]([F:37])([F:38])[F:36])=[CH:33][CH:34]=3)=[N:26][C:25]=2[CH3:39])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])=[CH:10][C:9]=1[CH3:40])([CH3:6])[C:4]([OH:42])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58906956HCID 58906956, compound

Product 1

HCID 58907068HCID 58907068, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of example 98 (400 mg, 0.68 mmol) in EtOH (20 mL) was added 1N NaOH (20 mL, 30 eq.) and the reaction was stirred at 85° C. for 2 h. When all of the starting material had disappeared, the reaction cooled, evaporated to dryness, taken up with water, neutralized with 1N HCL to pH 6 and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was chromatographed eluting with CH2Cl2 (100%) then CH2Cl2/MeOH (98/2) to afford the title compound as an oil (120 mg, 32%).

Workup

  1. temperaturethe reaction cooled
  2. customevaporated to dryness
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was chromatographed
  8. washeluting with CH2Cl2 (100%)

Sources & evidence

ORD record
ord-ea0f258a8a8a499cb0c68d941a4c2da6
Source dataset
uspto-grants-2007_07
Patent number
US07241793B2

Reaction notes

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