Acetic Acid → HCID 68537805, compound

HRID 1931388Notes

Reaction equation

HRID 1931388 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]([CH:15]=[CH:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.CO.C(O)(=O)C>[Pd].C1COCC1>[F:21][C:2]([F:1])([F:20])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:14][C:13]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 68537933HCID 68537933, compound

Product 1

HCID 68537805HCID 68537805, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

40 mg of 5% palladium on carbon were added to a solution of 416 mg (1.3 mmol) of 3-[5-(4-trifluoromethoxy-phenyl)-thiophen-2-yl]-acrylic acid in 20 ml of THF, and the reaction mixture was hydrogenated at atmospheric pressure and room temperature for 24 h. Then 10 ml of methanol and 40 mg of 5% palladium on carbon were added, and the reaction mixture was hydrogenated at atmospheric pressure and room temperature for further 24 hours. Then 10 ml of acetic acid were added, and the reaction mixture was hydrogenated at atmospheric pressure and room temperature for another 24 h. The mixture was filtered and evaporated under reduced pressure. The product was purified by preparative RP HPLC eluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA). After lyophilization, the product was obtained as a solid. Yield: 400 mg.

Workup

  1. waitthe reaction mixture was hydrogenated at atmospheric pressure and room temperature for further 24 hours
  2. waitthe reaction mixture was hydrogenated at atmospheric pressure and room temperature for another 24 h
  3. filtrationThe mixture was filtered
  4. customevaporated under reduced pressure
  5. customThe product was purified by preparative RP HPLC
  6. washeluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA)
  7. customAfter lyophilization, the product was obtained as a solid

Sources & evidence

ORD record
ord-943ff3b10d3341c2992576fd73564b93
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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