Sodium Hydroxide → HCID 59759344, compound

HRID 914343Notes

Reaction equation

HRID 914343 reaction equation
C([O:3][C:4](=[O:31])[C:5]([S:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][CH2:15][O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[N:13]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>CO.O1CCCC1>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:21]2[CH:20]=[CH:19][C:18]([CH2:17][O:16][CH2:15][CH2:14][C:12]3[N:13]=[C:9]([S:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:31])=[O:3])[S:10][CH:11]=3)=[CH:23][CH:22]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 597593242-[(4-{2-[(4'-Fluorobiphenyl-4-yl)methoxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid ethyl ester

Product 1

HCID 59759344HCID 59759344, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[(4-{2-[(4′-Fluorobiphenyl-4-yl)methoxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid ethyl ester (400 mg) synthesized in Example 155-3 was dissolved in methanol (4 mL) and tetrahydrofuran (4 mL), aqueous sodium hydroxide solution (1 mol/L, 2 mL) was added, and the mixture was stirred at room temperature for 4 hr. 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, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1 to 1:1) to give the title compound (245 mg) as a white solid.

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
  7. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-5626cb95ebad4d0293aa64a989e2b1c7
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

Loading…