Potassium Carbonate → HCID 59759010, compound

HRID 914294Notes

Reaction equation

HRID 914294 reaction equation
[C:1]([O:5][C:6](=[O:26])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:5][C:6](=[O:26])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:32][C:31]3[CH:34]=[CH:35][C:28]([Cl:27])=[CH:29][CH:30]=3)=[CH:23][CH:24]=2)[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 59759165HCID 59759165, compound

Product 1

HCID 59759010HCID 59759010, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-({4-[2-(4-Hydroxyphenoxy)ethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl ester (600 mg) obtained in Example 50-2 and 4-chlorobenzylbromide (312 mg) were dissolved in acetone (10 mL), potassium carbonate (210 mg) was added, and the mixture was refluxed for 6 hr. The reaction mixture was concentrated under reduced pressure, water 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=5:1) to give the title compound (420 mg) as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed for 6 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-11ccc6fbbcc242e1b7d0a3323d05f212
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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