Water → HCID 58451400, compound

HRID 456020Notes

Reaction equation

HRID 456020 reaction equation
[C:1]([O:5][C:6](=[O:20])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:19])[CH2:17]Cl)[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.[OH-].[Na+].O>C1(C)C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6](=[O:20])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:19])[CH2:17][O:34][C:31]2[CH:30]=[CH:29][C:28]([C:25]3[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=3)=[CH:33][CH:32]=2)[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 3454204-Fluoro-4'-hydroxybiphenylHCID 584514032-{[4-(Chloroacetyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 58451400HCID 58451400, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

2-{[4-(Chloroacetyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (23.8 g) and 4′-fluorobiphenyl-4-ol (12.00 g) obtained in Example 1 were dissolved in toluene (650 mL), aqueous sodium hydroxide solution (1 mol/L, 71 mL), tetrabutylammonium iodide (2.62 g) and water (71 mL) were added, and the mixture was heated under reflux for 3 hr, and allowed to cool to perform partitioning. The organic layer was washed twice with 1 mol/L aqueous sodium hydroxide solution (300 mL) and twice with saturated aqueous sodium chloride solution (200 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by column chromatography (Moritex Purif Pack SI 60 μm size 200 was used. elution solvent: hexane/ethyl acetate=95/5→70/30) to give the title compound as a pale-yellow oily substance (1.128 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. temperatureto cool
  4. customto perform partitioning
  5. washThe organic layer was washed twice with 1 mol/L aqueous sodium hydroxide solution (300 mL) and twice with saturated aqueous sodium chloride solution (200 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe obtained residue was purified by column chromatography (Moritex Purif Pack SI 60 μm size 200 was used. elution solvent: hexane/ethyl acetate=95/5→70/30)

Sources & evidence

ORD record
ord-37688475c70d4f4bac864351f8340bda
Source dataset
uspto-grants-2013_07
Patent number
US08497382B2

Reaction notes

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