Acetic Acid → L-Tartaric acid

HRID 1511851Notes

Reaction equation

HRID 1511851 reaction equation
C(O)(=O)C.[OH:5][C@H:6]([C@@H:10]([OH:14])[C:11]([OH:13])=[O:12])[C:7]([OH:9])=[O:8].COC([C@@]1(N)CC[C@H](C2C=CC(C#CCCCCCC)=CC=2)C1)=O>[OH-].[OH-].[Pd+2].O>[OH:5][C@H:6]([C@@H:10]([OH:14])[C:11]([OH:13])=[O:12])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86626581HCID 86626581, compound

Product 1

HCID 444305L-Tartaric acid

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Procedure

185 mg of palladium hydroxide on carbon (20% by weight) and acetic acid (25 mL, 0.44 mol) were loaded into a Parr shaker. (1R,3S)-1-Amino-3-(4-oct-1-ynyl-phenyl)-cyclopentanecarboxylic acid methyl ester; compound with (2R,3R)-2,3-dihydroxy-succinic acid (2.49 g, 0.00521 mol) was added and the reaction was evacuated, back-filled with nitrogen, followed by two cycles of evacuating and back-filling with hydrogen gas. The reaction was then pressurized to about 50 psi using hydrogen. The reaction was shaken at room temperature for about 50 minutes. The crude mixture was filtered through Celite® and washed with ethanol. The filtrate was concentrated, and the residue was brought up in a small amount of ethanol. Water was added. The mixture was nearly clear. The ethanol was removed under reduced pressure, and the remaining aqueous solution was left to stand. After a few minutes, needle-like crystals began to form. More water was added, and the mixture left to crystallize. The white solid was collected by filtration, and washed with water three times. The white solid was freeze-dried to remove remaining water. 1.9 g (90%) of (1R,3S)-1-amino-3-(4-octyl-phenyl)-cyclopentanecarboxylic acid methyl ester; compound with 0.5 equivalent of (2R,3R)-2,3-dihydroxy-succinic acid was obtained as fluffy white solid.

Workup

  1. customthe reaction was evacuated
  2. additionback-filled with nitrogen
  3. customof evacuating and back-filling with hydrogen gas
  4. filtrationThe crude mixture was filtered through Celite®
  5. washwashed with ethanol
  6. concentrationThe filtrate was concentrated
  7. additionWater was added
  8. customThe ethanol was removed under reduced pressure
  9. waitthe remaining aqueous solution was left
  10. waitAfter a few minutes
  11. customto form
  12. waitthe mixture left
  13. customto crystallize
  14. filtrationThe white solid was collected by filtration
  15. washwashed with water three times
  16. customThe white solid was freeze-dried
  17. customto remove

Sources & evidence

ORD record
ord-c049793cec074d5da0aab92ad275d40f
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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