HCID 68005991, compound → HCID 68006092, compound

HRID 1026598Notes

Reaction equation

HRID 1026598 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][C@H:8]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([O:25]CC2C=CC=CC=2)=[O:24])=[C:19]([F:33])[CH:18]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>[C].[Pd].C(O)C>[C:1]([O:5][C:6](=[O:34])[CH2:7][C@H:8]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[C:19]([F:33])[CH:18]=1)[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 68005991HCID 68005991, compound

Product 1

HCID 68006092HCID 68006092, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To an ethanol solution (80 ml) of benzyl 2′-{[(1R)-3-tert-butoxy-1-methyl-3-oxopropyl]oxy}-3-fluorobiphenyl-4-carboxylate (12.8 g) was added 10% palladium carbon (2.54 g), followed by stirring at room temperature for 7 hours under a hydrogen atmosphere. The reaction solution was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford 2′-{[(1R)-3-tert-butoxy-1-methyl-3-oxopropyl]oxy}-3-fluorobiphenyl-4-carboxylic acid (9.87 g).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-645fe976bf79466bb8c7f4e7a0edc779
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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