Acetic Acid → HCID 71294264, compound

HRID 1747551Notes

Reaction equation

HRID 1747551 reaction equation
[Si]([O:8][CH:9]([C:14]1[S:18][C:17]([C:19](=[O:21])[CH3:20])=[N:16][CH:15]=1)[C:10]([F:13])([F:12])[F:11])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[F:12][C:10]([F:11])([F:13])[CH:9]([C:14]1[S:18][C:17]([C:19](=[O:21])[CH3:20])=[N:16][CH:15]=1)[OH:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 71294185HCID 71294185, compound

Product 1

HCID 71294264HCID 71294264, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (3 mL) was dissolved 1-(5-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl) thiazol-2-yl)ethanone (356 mg, 1.05 mmol) obtained in Step 3. To the solution were added acetic acid (0.072 mL, 1.26 mmol) and tetrabutylammonium fluoride (1.0 mol/L solution in THF, 1.26 mL, 1.26 mmol) and the mixture was stirred at room temperature for 1 hour. A saturated aqueous sodium carbonate solution was added to the reaction mixture. Extraction with ethyl acetate, washing with a saturated aqueous ammonium chloride solution and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give Compound A46 (214 mg, 91%).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with a saturated aqueous ammonium chloride solution
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
  7. customto give Compound A46 (214 mg, 91%)

Sources & evidence

ORD record
ord-afe78c7830d94132a3f257885f727f93
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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