HCID 69211681, compound → 3-Carboxy-2-phenethyl-pentandioic acid 5-tert-butyl ester 1-methyl ester

HRID 902921Notes

Reaction equation

HRID 902921 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH:4]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:5]([C:14]([O:16]CC1C=CC=CC=1)=[O:15])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:32])[CH:4]([CH2:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH:5]([C:14]([OH:16])=[O:15])[CH2:6][C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8]

Participants

4

Reactant 1

HCID 69211681HCID 69211681, compound

Product 1

HCID 692123143-Carboxy-2-phenethyl-pentandioic acid 5-tert-butyl ester 1-methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the compound of example 52 (700 mg, 1.59 mmol) in ethanol (95%, 100 mL) was hydrogenated in the presence of a catalytic amount palladium (10% on charcoal). After 24 h of stirring, the reaction was complete. The mixture was filtered over a celite pad and the solvent was evaporated. The residue was distributed between ethyl acetate and water. The aqueous phase was extracted twice more with ethyl acetate. The recombined organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated.

Workup

  1. filtrationThe mixture was filtered over a celite pad
  2. customthe solvent was evaporated
  3. extractionThe aqueous phase was extracted twice more with ethyl acetate
  4. washThe recombined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-86422dc6957e4e9f8d1844177c1d3064
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

Loading…