Sodium Hydroxide → HCID 58906942, compound

HRID 1295101Notes

Reaction equation

HRID 1295101 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[S:29][C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)=[N:27][C:26]=2[CH3:40])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=[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[S:29][C:28]([C:30]3[CH:31]=[CH:32][C:33]([C:36]([F:38])([F:39])[F:37])=[CH:34][CH:35]=3)=[N:27][C:26]=2[CH3:40])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=[CH:10][C:9]=1[CH3:41])([CH3:6])[C:4]([OH:43])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58907082HCID 58907082, compound

Product 1

HCID 58906942HCID 58906942, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of example 96 (450 mg, 0.29 mmol) in EtOH (20 mL) was added 1N NaOH (0.9 mL, 3 eq.) and the reaction was stirred at 85° C. for 1 h. When all of the starting material had disappeared, the reaction cooled, evaporated to dryness, taken up with 1N HCl, extracted with CH2Cl2 and washed with water. The organic phase was dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was chromatographed eluting with CH2Cl2 (100%) to afford the title compound as a yellow solid (60 mg, 34%).

Workup

  1. temperaturethe reaction cooled
  2. customevaporated to dryness
  3. extractionextracted with CH2Cl2
  4. washwashed with water
  5. dry with materialThe organic phase was 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-a6a474c669b34da690b26f0961172059
Source dataset
uspto-grants-2007_07
Patent number
US07241793B2

Reaction notes

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