3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-acrylic Acid Ethyl Ester → 3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-propionic Acid Ethyl Ester

HRID 11657

Reaction equation

HRID 11657 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH:5]=[CH:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[O:14][CH2:15][C:16]([N:18]1[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:20][C@H:19]1[CH3:33])=[O:17])[CH3:2].[H][H]>C(OCC)(=O)C.[Pt](=O)=O>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[O:14][CH2:15][C:16]([N:18]1[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[CH2:20][C@H:19]1[CH3:33])=[O:17])[CH3:2]

Participants

5

Reactant 2

HCID 696554333-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-acrylic Acid Ethyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 696552783-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-propionic Acid Ethyl EsterYield 95.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-acrylic acid ethyl ester (0.50 g, 1.0 mmol) in ethyl acetate(15 mL) in a Parr bottle was added platinum dioxide on carbon (0.25 g, 5% on carbon). The mixture was shaken under a positive pressure of hydrogen at 30 psi for 15 minutes at ambient temperature. The mixture was filtered through a pad of celite and concentrated to give the title compound (0.47 g).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-578c7de0a9fb4ee387e66e7e36fa0dea
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

Loading…