(R,S)-3-[4-(1-benzyloxycarbonyl-ethoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester → HCID 69419465, compound

HRID 1353262Notes

Reaction equation

HRID 1353262 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C@H:5]([O:26][CH2:27][CH3:28])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C@H:14]([C:16]([O:18]CC2C=CC=CC=2)=[O:17])[CH3:15])=[CH:9][CH:8]=1)[CH3:2]>CCO.O.[Pd]>[CH2:1]([O:3][C:4](=[O:29])[C@H:5]([O:26][CH2:27][CH3:28])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C@H:14]([C:16]([OH:18])=[O:17])[CH3:15])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 1

HCID 69418001(R,S)-3-[4-(1-benzyloxycarbonyl-ethoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester

Product 1

HCID 69419465HCID 69419465, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of (R,S)-3-[4-(1-benzyloxycarbonyl-ethoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester (1.05 g, 2.63 mmol) in EtOH (20 ml) and H2O (0.5 ml) was added a slurry of Pd—C (5%, 100 mg) in EtOH (10 ml). The suspension was hydrogenated under balloon pressure for 2 hours. The mixture was filtered through a pad of celite and concentrated to a residue, the residue was then purified by silica gel chromatography with EtOAc/Hexanes (25% to 100%) to afford the acid product (550 mg, 68%).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated to a residue
  3. customthe residue was then purified by silica gel chromatography with EtOAc/Hexanes (25% to 100%)

Sources & evidence

ORD record
ord-befcfd5f3eb447f393148c8ee677a3fd
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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