HCID 68510882, compound → HCID 59028778, compound

HRID 1715055Notes

Reaction equation

HRID 1715055 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]=[CH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)(=[O:19])=[O:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH3:2]>CO.C(O)(=O)C.CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)(=[O:18])=[O:19])=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

6

Reactant 1

HCID 68510882HCID 68510882, compound

Product 1

HCID 59028778HCID 59028778, compoundYield 99.5%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[6-(3-Fluoro-benzenesulfonyl)-naphthalen-1-yl]-acrylic acid ethyl ester (2.0 g) was dissolved in a mixture of methanol (20 mL), acetic acid (20 mL) and EtOAc (50 mL) in a Parr vessel. Palladium on activated carbon (1.0 g, 10% Pd) was added, and the vessel was purged with nitrogen. The reaction mixture was stirred at room temperature under 60 atm (4.14 Bar) hydrogen for 18 hours. The vessel was purged with nitrogen, and the reaction mixture was removed and filtered through Celite. The filtrate was evaporated under reduced pressure to give 2.0 g of 3-[6-(3-fluoro-benzenesulfonyl)-naphthalen-1-yl]-propionic acid ethyl ester.

Workup

  1. customthe vessel was purged with nitrogen
  2. customThe vessel was purged with nitrogen
  3. customthe reaction mixture was removed
  4. filtrationfiltered through Celite
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-06abcf54d28847f68d23c0eb1f78e44f
Source dataset
uspto-grants-2010_09
Patent number
US07799797B2

Reaction notes

Loading…