Acetic Acid → 3-[5-(4-Fluoro-phenyl)-thiophen-2-yl]-propionic acid

HRID 1931391Notes

Reaction equation

HRID 1931391 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CO.C(O)(=O)C>[Pd].O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 534120103-[5-(4-Fluoro-phenyl)-thiophen-2-yl]-acrylic acid

Product 1

HCID 685366543-[5-(4-Fluoro-phenyl)-thiophen-2-yl]-propionic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

40 mg of 5% palladium on carbon were added to a solution of 500 mg (2.0 mmol) of 3-[5-(4-fluoro-phenyl)-thiophen-2-yl]-acrylic acid in 20 ml of tetrahydrofuran, and the reaction mixture was hydrogenated at atmospheric pressure and room temperature for 24 h. 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. 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, and 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
  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-aa7e0e955ce84d579f2f86795143aa50
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

Loading…