3-{4-[1-Allyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid methyl ester → 3-{4-[1-Propyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-butyl]-benzoylamino}-propionic acid methyl ester

HRID 658301Notes

Reaction equation

HRID 658301 reaction equation
[CH3:1][O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7](=[O:39])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH2:36][CH:37]=[CH2:38])([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:15][CH:16]=[CH2:17])=[CH:10][CH:9]=1>CCO.[Pd]>[CH3:1][O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7](=[O:39])[C:8]1[CH:9]=[CH:10][C:11]([C:14]([CH2:36][CH2:37][CH3:38])([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=3)=[CH:22][CH:21]=2)[CH2:15][CH2:16][CH3:17])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 674857653-{4-[1-Allyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 674861843-{4-[1-Propyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-butyl]-benzoylamino}-propionic acid methyl esterYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-{4-[1-allyl-1-(4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid methyl ester (0.0731 g, 0.126 mmol) in EtOH (4.0 mL) is treated with 10% palladium on carbon (16 mg), flushed with hydrogen, and stirred under 1 atm pressure overnight. The mixture is then filtered through Celite® and concentrated to provide 0.0703 g (96%) of the title compound as a clear syrup. MS (ES): 84.4 [M+H]+.

Workup

  1. customflushed with hydrogen
  2. filtrationThe mixture is then filtered through Celite®
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e6082c2daf7e414ab9bcff6172e95218
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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