HCID 59356031, compound → HCID 59355985, compound

HRID 660993Notes

Reaction equation

HRID 660993 reaction equation
[CH3:1][O:2][C:3](=[O:41])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([C:14]([CH2:38][CH:39]=[CH2:40])([CH2:18][O:19][C:20]2[CH:25]=[C:24]([CH3:26])[C:23]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)=[C:22]([CH3:37])[CH:21]=2)[CH2:15][CH:16]=[CH2:17])=[CH:12][CH:13]=1)=[O:8]>CCO.[Pd]>[CH3:1][O:2][C:3](=[O:41])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([C:14]([CH2:18][O:19][C:20]2[CH:25]=[C:24]([CH3:26])[C:23]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=3)=[C:22]([CH3:37])[CH:21]=2)([CH2:15][CH2:16][CH3:17])[CH2:38][CH2:39][CH3:40])=[CH:12][CH:13]=1)=[O:8]

Participants

4

Reactant 1

HCID 59356031HCID 59356031, compound

Product 1

HCID 59355985HCID 59355985, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-({5-[1-allyl-1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (0.0679 g, 0.116 mmol) in EtOH (2.0 mL) is treated with 10% palladium on carbon (12 mg), flushed with H2, and stirred under 1 atm pressure for 2 h. The mixture is then filtered through Celite® and conc. to provide 3-({5-[1-(2,6-Dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-1-propyl-butyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (0.0591 g, 86%) as a white foam. MS (ES): 588.4 [M−H]−.

Workup

  1. customflushed with H2
  2. filtrationThe mixture is then filtered through Celite®

Sources & evidence

ORD record
ord-1cd3f59026f046d8906525a02eb88863
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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