HCID 86593274, compound → HCID 22261925, compound

HRID 1610596Notes

Reaction equation

HRID 1610596 reaction equation
[OH:1][CH:2]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[CH:30][CH:29]=1)[CH:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:16]=1)[C:4]([O:6]CC1C=CC=CC=1)=[O:5].[H][H]>C(O)C.[Pd]>[OH:1][CH:2]([C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[CH:32][CH:33]=1)[CH:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:16]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 86593274HCID 86593274, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22261925HCID 22261925, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl (2RS,3RS)-3-hydroxy-3-[4-(pyridin-2-yloxy)phenyl]-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (4.99 g, 8.95 mmol) in ethanol (500 ml) was added 10% palladium/carbon (containing water by 50%, 500 mg), and the mixture was stirred under a 1 atm hydrogen stream for 2 hrs. The reaction solution was filtered with celite and the filtrate was concentrated to give the objective substance (4.50 g, 100%, crude). The present compound was used for the next reaction as a crude compound.

Workup

  1. filtrationThe reaction solution was filtered with celite
  2. concentrationthe filtrate was concentrated
  3. customto give the objective substance (4.50 g, 100%, crude)

Sources & evidence

ORD record
ord-a5e3c782ebf94a17a3fd61a6c087b8a6
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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