Acetic Acid → Methyl 2-acetamido-3-oxobutanoate

HRID 1428988Notes

Reaction equation

HRID 1428988 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C:4](=[N:8]O)[C:5](=[O:7])[CH3:6].[C:11](O)(=[O:13])[CH3:12]>C(OC(=O)C)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:10])[CH:4]([NH:8][C:11](=[O:13])[CH3:12])[C:5](=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178501737HCID 178501737, compound

Product 1

HCID 11084356Methyl 2-acetamido-3-oxobutanoateYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

Part B: Crude 2-hydroxyimino-3-oxo-butyric acid methyl ester (24 gram, ˜0.15 mol) dissolved in a magnetically stirred mixture of acetic acid (293 ml), acetic acid anhydride (110 ml) and Pd/C (4 gram) was hydrogenated for 20 hours at room temperature at 1 atmosphere H2 pressure. After filtration over hyflo, the acetic acid and acetic acid anhydride were removed by concentration in vacuo. The resulting crude mixture was purified by flash chromatography (dichloromethane/methanol=95/5 (v/v)) to give 2-acetylamino-3-oxo-butyric acid methyl ester (16.7 gram, 60% yield) as a white solid. Rf (dichloromethane/methanol=95/5 (v/v))=0.4. 1H-NMR (400 MHz, CDCl3): 2.08 (s, 3H), 2.40 (s, 3H), 3.83 (s, 3H), 5.29 (d, J˜7, 1H), 6.71 (br s, 1H).

Workup

  1. filtrationAfter filtration over hyflo
  2. customthe acetic acid and acetic acid anhydride were removed by concentration in vacuo
  3. customThe resulting crude mixture was purified by flash chromatography (dichloromethane/methanol=95/5 (v/v))

Sources & evidence

ORD record
ord-46ba7d3bdf4844839bedfa9477c82183
Source dataset
uspto-grants-2015_01
Patent number
US08937184B2

Reaction notes

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