Sodium Hydroxide → HCID 10117639, compound

HRID 2116609Notes

Reaction equation

HRID 2116609 reaction equation
C([O:3][C:4](=[O:36])[C:5]([CH3:35])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH: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])=[C:24]([F:32])[CH:23]=3)=[N:19][C:18]=2[CH3:33])[CH3:16])=[CH:10][C:9]=1[CH3:34])[CH3:6])C.[OH-].[Na+]>CCO>[CH3:6][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([C:17]2[S:21][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[C:24]([F:32])[CH:23]=3)=[N:19][C:18]=2[CH3:33])[CH3:16])=[CH:10][C:9]=1[CH3:34])([CH3:35])[C:4]([OH:36])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10229998HCID 10229998, compound

Product 1

HCID 10117639HCID 10117639, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of example 6 (270 mg) in EtOH (15 mL) was treated with 1N sodium hydroxide (1.54 mL, 3 eq.) and the mixture heated to reflux for 3 hours. The cooled reaction was concentrated and the residue diluted with water (20 mL); 1N hydrochloric acid (2 mL) was added and the resulting suspension extracted with dichloromethane (20 mL). The organic extract was dried over magnesium sulphate and concentrated to give the title compound in 74% yield as a yellow solid (190 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 3 hours
  3. customThe cooled reaction
  4. concentrationwas concentrated
  5. additionthe residue diluted with water (20 mL)
  6. addition1N hydrochloric acid (2 mL) was added
  7. extractionthe resulting suspension extracted with dichloromethane (20 mL)
  8. extractionThe organic extract
  9. dry with materialwas dried over magnesium sulphate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-1918938a58d1488d9d2b4827540dde8b
Source dataset
uspto-grants-2008_10
Patent number
US07439259B2

Reaction notes

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