Sodium Hydroxide → HCID 58907001, compound

HRID 1295105Notes

Reaction equation

HRID 1295105 reaction equation
C([O:3][C:4](=[O:43])[C:5]([CH3:42])([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:25]2[N:26]([CH3:40])[N:27]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)[CH:29]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[CH:10][C:9]=1[CH3:41])[CH3:6])C.[OH-].[Na+]>CCO>[CH3:42][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:25]2[N:26]([CH3:40])[N:27]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:38])([F:37])[F:39])=[CH:32][CH:31]=3)[CH:29]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[CH:10][C:9]=1[CH3:41])([CH3:6])[C:4]([OH:43])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58907041HCID 58907041, compound

Product 1

HCID 58907001HCID 58907001, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of example 106 (280 mg, 0.49 mmol) in EtOH (20 mL) was added excess of a 1N NaOH solution and the mixture was stirred at 50° C. for 2 h. The reaction was cooled, evaporated to dryness, the residue taken up with water, neutralized with 1N HCl to pH 7 and then extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and the solvent removed under vacuum. The residue was then chromatographed eluting with CH2Cl2 (100%), CH2Cl2/MeOH (99/1), CH2Cl2/MeOH (98/2) and finally CH2Cl2/MeOH (96/4) to afford the title compound as an oil (60 mg, 22%).

Workup

  1. temperatureThe reaction was 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 under vacuum
  7. customThe residue was then chromatographed
  8. washeluting with CH2Cl2 (100%), CH2Cl2/MeOH (99/1), CH2Cl2/MeOH (98/2) and finally CH2Cl2/MeOH (96/4)

Sources & evidence

ORD record
ord-1fcd8fa057484198b5a6e7bd90ef719e
Source dataset
uspto-grants-2007_07
Patent number
US07241793B2

Reaction notes

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