Sodium Hydroxide → HCID 58907033, compound

HRID 1295103Notes

Reaction equation

HRID 1295103 reaction equation
C([O:3][C:4](=[O:35])[C:5]([CH3:34])([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:17]2[S:21][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[N:19][C:18]=2[CH3:32])[CH3:16])=[CH:10][C:9]=1[CH3:33])[CH3:6])C.[OH-].[Na+]>CCO>[CH3:34][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:17]2[S:21][C:20]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:27]=3)=[N:19][C:18]=2[CH3:32])[CH3:16])=[CH:10][C:9]=1[CH3:33])([CH3:6])[C:4]([OH:35])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58907088HCID 58907088, compound

Product 1

HCID 58907033HCID 58907033, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of example 102 (50 mg, 0.5 mmol) in EtOH (20 mL) was added excess of a 1N NaOH solution and the mixture was stirred at 60° 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%) then CH2Cl2/MeOH (98/2) and finally CH2Cl2/MeOH (95/5) to afford the title compound as an oil (10 mg, 20%).

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%)

Sources & evidence

ORD record
ord-c6c38680f5d94ca7a2696adb59326e79
Source dataset
uspto-grants-2007_07
Patent number
US07241793B2

Reaction notes

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