Cesium carbonate → HCID 69141086, compound

HRID 854556Notes

Reaction equation

HRID 854556 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.[CH2:13]([C:15]1[S:19][C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[N:17][C:16]=1[CH2:30][CH2:31]OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:31][CH2:30][C:16]2[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[S:19][C:15]=2[CH2:13][CH3:14])[CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 39129Methyl 3-HydroxyphenylacetateHCID 58934100HCID 58934100, compound

Product 1

HCID 69141086HCID 69141086, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3-Hydroxy-phenyl)-acetic acid methyl ester (166 mg, 1.0 mmol) is dissolved into anhydrous acetonitrile (ACN) (5 mL). Toluene-4-sulfonic acid 2-[5-ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethyl ester (432 mg, 0.950 mmol) is added to the reaction, followed by the addition of cesium carbonate (652 mg, 2.00 mmol). The reaction is allowed to stir under nitrogen at room temperature and monitored by TLC and HPLC. Upon complete consumption of the tosylate, the reaction is diluted with diethyl ether and quenched with 0.1N NaOH. The two phases are separated, then the organic layer washed with water and brine. The organic phase is dried over anhydrous sodium sulfate and concentrated under vacuum. The residue is further purified using either EtOAc/Hexanes (1:9) or Acetone/Hexanes (1:9) gradients on silica gel chromatography to yield (3-{2-[5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-phenyl)-acetic acid methyl ester (140 mg, 0.311 mmol) or 33%.

Workup

  1. customUpon complete consumption of the tosylate
  2. additionthe reaction is diluted with diethyl ether
  3. customquenched with 0.1N NaOH
  4. customThe two phases are separated
  5. washthe organic layer washed with water and brine
  6. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue is further purified

Sources & evidence

ORD record
ord-d9936d774a0b4533befbd9f05e1e1260
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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