Sodium Hydroxide → HCID 59759162, compound

HRID 914312Notes

Reaction equation

HRID 914312 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][C:14]1[N:15]=[C:16]([S:19][C:20]([CH3:29])([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[S:17][CH:18]=1)=[O:4].[OH-].[Na+]>CO.O1CCCC1>[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:7]2[CH:8]=[CH:9][C:10]([O:11][CH2:12][CH2:13][C:14]3[N:15]=[C:16]([S:19][C:20]([CH3:29])([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[S:17][CH:18]=3)=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59758832HCID 59758832, compound

Product 1

HCID 59759162HCID 59759162, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(2-{2-[(2-tert-Butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethoxy)-4′-fluoro-biphenyl-3-carboxylic acid methyl ester (1.6 g) synthesized in Example 92-2 was dissolved in methanol (15 mL) and tetrahydrofuran (20 mL), aqueous sodium hydroxide solution (1 mol/L, 15 ml) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, aqueous 10% citric acid solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.3 g) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, aqueous 10% citric acid solution
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aca1a69b8e2c430fbd4da1250eee3f7e
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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