HCID 86593292, compound → HCID 22261471, compound

HRID 1610684Notes

Reaction equation

HRID 1610684 reaction equation
[OH:1][CH:2]([C:28]1[CH:33]=[CH:32][C:31]([C:34]([O:36][CH3:37])=[O:35])=[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]>C(O)C.[Pd]>[OH:1][CH:2]([C:28]1[CH:33]=[CH:32][C:31]([C:34]([O:36][CH3:37])=[O:35])=[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]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 86593292HCID 86593292, compound

Product 1

HCID 22261471HCID 22261471, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of benzyl (2RS,3RS)-3-hydroxy-3-[4-(methoxycarbonyl)phenyl]-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propionate (69.90 g, 134.3 mmol) in ethanol (200 ml) was hydrogenated overnight using 10% palladium/carbon (containing water by 50%). (5 g) as a catalyst under normal pressure. The catalyst was removed by filtration, washed with ethanol, and the solvent of the recovered filtrate was evaporated under reduced pressure to give crude (2RS,3RS)-3-hydroxy-3-[4-(methoxycarbonyl)phenyl]-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propionic acid as a colorless foam.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethanol
  3. customthe solvent of the recovered filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-09851f3182314b33a29203095ea83ae7
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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