HCID 86598009, compound → HCID 86598008, compound

HRID 970056Notes

Reaction equation

HRID 970056 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]([NH:5][C@H:6]([CH2:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][CH:13]=1)[C:7]([OH:9])=[O:8])=[O:4]>CC(O)=O.[Pd]>[F:1][C:2]([F:27])([F:28])[C:3]([NH:5][C@H:6]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:16][CH:17]=1)[C:7]([OH:9])=[O:8])=[O:4]

Participants

4

Reactant 1

HCID 86598009HCID 86598009, compound

Product 1

HCID 86598008HCID 86598008, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 8.7 g (21.7 mmol) of 2-(R)-trifluoroacetamido-4-oxo-4-(4-octylphenyl)butanoic acid (from Example 12, Step A) and 1.75 g of 10% Pd/C in 25 mL of HOAc was hydrogenated at 40 psi for 20 h. The mixture was filtered through a pad of Celite; the flask and pad were rinsed with EtOAc. Toluene was added to the filtrate and the filtrate was concentrated to afford 9.0 of the title compound which was used without further purification.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washthe flask and pad were rinsed with EtOAc
  3. additionToluene was added to the filtrate
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fa6e7d4e14c748619d13a257f51b27a3
Source dataset
uspto-grants-2007_12
Patent number
US07309721B2

Reaction notes

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