3-[4-(2-Benzyloxy-acetoxy)-phenyl]-2-{3-[4-(2-benzyloxy-acetoxy)-phenyl]propionyl amino}-propionic acid methyl ester → 3-[4-(2-Hydroxy-acetoxy)-phenyl]-2-{3-[4-(2-hydroxy-acetoxy)-phenyl]-propionylamino}-propionic acid methyl ester

HRID 2090586Notes

Reaction equation

HRID 2090586 reaction equation
[CH3:1][O:2][C:3](=[O:47])[CH:4]([NH:24][C:25](=[O:46])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35](=[O:45])[CH2:36][O:37]CC2C=CC=CC=2)=[CH:30][CH:29]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:23])[CH2:14][O:15]CC2C=CC=CC=2)=[CH:8][CH:7]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:47])[CH:4]([NH:24][C:25](=[O:46])[CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35](=[O:45])[CH2:36][OH:37])=[CH:32][CH:33]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13](=[O:23])[CH2:14][OH:15])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 584275113-[4-(2-Benzyloxy-acetoxy)-phenyl]-2-{3-[4-(2-benzyloxy-acetoxy)-phenyl]propionyl amino}-propionic acid methyl ester

Product 1

HCID 167395763-[4-(2-Hydroxy-acetoxy)-phenyl]-2-{3-[4-(2-hydroxy-acetoxy)-phenyl]-propionylamino}-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-[4-(2-Benzyloxy-acetoxy)-phenyl]-2-{3-[4-(2-benzyloxy-acetoxy)-phenyl]propionyl amino}-propionic acid methyl ester 25 (10 grams, 15.64 mmol) is dissolved in ethyl acetate (100 mL) in a pressure vessel, palladium on carbon (10%, 5 grams) is added and the mixture is stirred under an atmosphere of hydrogen (4 Kg) for 5 hours. The catalyst is removed by filtration and is distilled of the ethyl acetate. The crude 26 can be purified in appropriate solvent.

Workup

  1. customThe catalyst is removed by filtration
  2. distillationis distilled of the ethyl acetate
  3. customThe crude 26 can be purified in appropriate solvent

Sources & evidence

ORD record
ord-fa34604592e34d1b9398b703835f4166
Source dataset
uspto-grants-2013_05
Patent number
US08436201B2

Reaction notes

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