Sodium Hydroxide → HCID 58907104, compound

HRID 1295100Notes

Reaction equation

HRID 1295100 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]=[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[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]=[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 58906949HCID 58906949, compound

Product 1

HCID 58907104HCID 58907104, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of example 94 (520 mg, 0.85 mmol) in EtOH (20 mL) was added 1N NaOH (2.5 mL, 3 eq.) and the reaction was stirred at 80° C. for 1 h. When all of the starting material had disappeared, the reaction cooled, evaporated to dryness, taken up with 1 N HCl and extracted with CH2Cl2. The organic phase was dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was chromatographed eluting with CH2Cl2 (100%) then CH2Cl2/MeOH (95/5) to afford the title compound as a yellow oil (80 mg, 16%).

Workup

  1. temperaturethe reaction cooled
  2. customevaporated to dryness
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic phase 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-90436345726f41cd920194c977e5abc1
Source dataset
uspto-grants-2007_07
Patent number
US07241793B2

Reaction notes

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