Sodium Hydroxide → HCID 58906999, compound

HRID 1295098Notes

Reaction equation

HRID 1295098 reaction equation
C([O:3][C:4](=[O:40])[C:5]([CH3:39])([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:22]2[S:26][C:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)=[N:24][C:23]=2[CH3:37])[CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][C:9]=1[CH3:38])[CH3:6])C.[OH-].[Na+]>CCO>[CH3:39][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:22]2[S:26][C:25]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:35])([F:36])[F:34])=[CH:31][CH:32]=3)=[N:24][C:23]=2[CH3:37])[CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][C:9]=1[CH3:38])([CH3:6])[C:4]([OH:40])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58906936HCID 58906936, compound

Product 1

HCID 58906999HCID 58906999, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of example 90 (780 mg, 1.32 mmol) in EtOH (20 mL) was added 1N NaOH (4 mL, 3 eq.) and the reaction was stirred at 80° C. for 2h. When all of the starting material had disappeared, the reaction cooled, evaporated to dryness, taken up with 1N HCl, extracted with CH2Cl2 and the organic phase washed with water. The organic layer was then dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was chromatographed eluting with CH2Cl2 (100%) then CH2Cl2/MeOH (90/10) to afford the title compound as a yellow solid (410 mg, 55.4%).

Workup

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

Sources & evidence

ORD record
ord-81dd791527224117958c941bf6a6a505
Source dataset
uspto-grants-2007_07
Patent number
US07241793B2

Reaction notes

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