HCID 57907565, compound → 2-(2-Oxo-1,3-oxazolidin-3-yl)propanoic acid

HRID 1947730Notes

Reaction equation

HRID 1947730 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]([CH3:18])[C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH2:5][CH2:4][O:3]1.[H][H]>[Pd].C(O)C>[O:1]=[C:2]1[N:6]([CH:7]([CH3:18])[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][O:3]1

Participants

5

Reactant 2

HCID 57907565HCID 57907565, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 431321042-(2-Oxo-1,3-oxazolidin-3-yl)propanoic acidYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A 25 mL round bottom flask under an atmosphere of nitrogen was charged with 0.030 g (0.028 mmol) of 10 weight percent palladium on activated carbon and wet with 2 mL of ethanol. Next, a solution of 0.37 g (1.5 mmol) of benzyl 2-(2-oxo-1,3-oxazolidin-3-yl)propanoate from step B above in 10 mL of ethanol was added and the mixture placed under 1 atmosphere of hydrogen. The reaction was stirred for 3 h then filtered through a pad of Celite®. The pad was washed with 20 mL of ethanol and the filtrate was evaporated in vacuo to afford the title compound as a colorless solid (0.24 g, quantitative yield). 1H-NMR (500 MHz, CD3OD) δ: 4.60-4.30 (m, 3H), 3.80-3.60 (m, 2H), 1.45 (d, J=3.5, 3H). LC-MS: m/z (ES) 160 (MH)+.

Workup

  1. filtrationthen filtered through a pad of Celite®
  2. washThe pad was washed with 20 mL of ethanol
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-f17c7cdda624488a9c8c2af35f78dae5
Source dataset
uspto-grants-2013_03
Patent number
US08399480B2

Reaction notes

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