HCID 66653360, compound → HCID 66653136, compound

HRID 1524274Notes

Reaction equation

HRID 1524274 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C@@H:11]([C:13]([O:15]CC2C=CC=CC=2)=[O:14])[CH3:12])[CH:5]=1>CO.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C@@H:11]([C:13]([OH:15])=[O:14])[CH3:12])[CH:5]=1

Participants

4

Reactant 1

HCID 66653360HCID 66653360, compound

Product 1

HCID 66653136HCID 66653136, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Add palladium hydroxide (3.0 g, 21 mmol) to a solution of 3-((R)-1-benzyloxycarbonyl-ethoxy)-benzoic acid methyl ester (14 g, 45 mmol) in MeOH (400 mL). De-gas the mixture with Argon for 10 minutes then place under 60 psi of hydrogen. Shake the vessel for 2 hours. Filter the mixture through a pad of diatomaceous earth and concentrate under reduced pressure. Triturate the residue with a mixture of hexanes and methylene chloride to provide 7.5 g of 3-((R)-1-carboxy-ethoxy)-benzoic acid methyl ester as a solid.

Workup

  1. customDe-gas the mixture with Argon for 10 minutes
  2. filtrationFilter the mixture through a pad of diatomaceous earth
  3. concentrationconcentrate under reduced pressure
  4. customTriturate the residue
  5. additionwith a mixture of hexanes and methylene chloride

Sources & evidence

ORD record
ord-eed0688c3acc4125a6efc1662a949531
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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