Oxalic acid dihydrate → (2S)-2-ethoxy-3-(4-hydroxy-2-methoxy-phenyl)-propionic acid methyl ester

HRID 1064964Notes

Reaction equation

HRID 1064964 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@@H:4]([O:23][CH2:24][CH3:25])[C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][C:8]=1[O:21][CH3:22])O.O.O.C(O)(=O)C(O)=O>C(O)(C)C.[Pd]>[CH3:1][O:2][C:3](=[O:26])[C@@H:4]([O:23][CH2:24][CH3:25])[CH2:5][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[O:21][CH3:22]

Participants

5

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 68616136(2S,3R)-3-(4-benzyloxy-2-methoxy-phenyl)-2-ethoxy-3-hydroxy-propionic acid methyl ester

Product 1

HCID 68617310(2S)-2-ethoxy-3-(4-hydroxy-2-methoxy-phenyl)-propionic acid methyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of (2S,3R)-3-(4-benzyloxy-2-methoxy-phenyl)-2-ethoxy-3-hydroxy-propionic acid methyl ester (100 mg, 200 μmol) and oxalic acid dihydrate (150 mg, 1.2 mmol) in isopropanol (2 ml) was hydrogenated at a pressure of 50 atmospheres over 10% palladium on charcoal (20 mg) at ambient temperature for 6.5 h. The catalyst was filtered off and the solvent evaporated under reduced pressure. The residue was dissolved in ice water/aqueous sodium bicarbonate solution 1/1 and extracted two times with ethyl acetate. The combined extracts were washed two times with ice water/brine 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure to give a yellow liquid which was purified by column chromatography (silica gel, cyclohexane/AcOEt) to yield 43 mg (170 μmol, 85%) of the title compound as light yellow liquid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ice water/aqueous sodium bicarbonate solution 1/1
  4. extractionextracted two times with ethyl acetate
  5. washThe combined extracts were washed two times with ice water/brine 1/1
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customto give a yellow liquid which
  9. customwas purified by column chromatography (silica gel, cyclohexane/AcOEt)

Sources & evidence

ORD record
ord-9d8f38e0ef054ec595f5686f47c8a5c4
Source dataset
uspto-grants-2005_11
Patent number
US06969725B2

Reaction notes

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