4-[N-dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino] butanoic acid, ethyl ester → 4-[N-Dodecyl-N-2-[4-[3-hydroxy-4,4,4-trifluorobutyl]phenoxy]ethylamino]butanoic acid, ethyl ester

HRID 1700893Notes

Reaction equation

HRID 1700893 reaction equation
[CH2:1]([N:13]([CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[CH:25]([OH:30])[C:26]([F:29])([F:28])[F:27])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>[Pd].C(OCC)(=O)C>[CH2:1]([N:13]([CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][CH:25]([OH:30])[C:26]([F:27])([F:28])[F:29])=[CH:21][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 1

HCID 867571214-[N-dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino] butanoic acid, ethyl ester

Product 1

HCID 867571234-[N-Dodecyl-N-2-[4-[3-hydroxy-4,4,4-trifluorobutyl]phenoxy]ethylamino]butanoic acid, ethyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[N-dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino] butanoic acid, ethyl ester (3.5 g, 6.46 mmol), palladium on activated carbon (10%, 0.6 g) and ethyl acetate (250 ml) was hydrogenated under 30 psi for 6 h. After filtration, the solvent was removed in vacuo to give the title compound (3.3 g, 94%) as a colorless oil.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-76e8fa7313f74a5f9d176655cf45ad08
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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