2,3-Dihydroxybutanedioic Acid → HCID 13557624, compound

HRID 1883521Notes

Reaction equation

HRID 1883521 reaction equation
[N:1]1C=C[CH:4]=[CH:3][CH:2]=1.[C:7](Cl)(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[OH-].[Na+].[C:29]([OH:38])(=[O:37])[CH:30]([CH:32]([C:34](O)=O)[OH:33])O>C1COCC1.C(O)C.CO>[C:7]([NH:1][C:2]1[CH:34]=[C:32]([OH:33])[C:30](=[CH:4][CH:3]=1)[C:29]([OH:38])=[O:37])(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

8

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 1049PyridineHCID 14798Sodium HydroxideHCID 5702750HCID 5702750, compound2×

Product 1

HCID 13557624HCID 13557624, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of PAS (2.6 g, 17 mmol) in 100 ml anhydrous THF and 4 ml pyridine was added dropwise a solution of elaidic acid chloride (5.11 g, 17 mmol) in 20 ml THF at 0° C. The reaction mixture was stirred at ambient temperature for 24 hours. More elaidic acid chloride (1.0 g) was added, and after 4 hours, a small amount methanol was added. The solvents were evaporated at high, vacuum, and the residue was partitioned between ether and water. The organic phasewas washed with tartaric acid (aq) and water. The solvent was evaporated off, and the residue was dissolved in 100 ml methanol to which was added 5 ml water. The solid deposit was filtered off and recrystallised from ethanol to give 3.9 g crude material 1.5 g of this material was dissolved in 100 ml ethanol to which was added 11 ml 1M NaOH(aq). The mixture was stirred at ambient temperature for 2 hours and acidified with 30 ml 0.5M tartaric acid(aq). The solid deposit was washed with water, dissolved in ether, and the organic phase washed with tartaric acid(aq). The solvent was evaporated off, and the residue was evaporated from anhydrous chloroform×2, to give 1.3 g(87%) of the title compound.

Workup

  1. waitafter 4 hours
  2. customThe solvents were evaporated at high, vacuum
  3. customthe residue was partitioned between ether and water
  4. washThe organic phasewas washed with tartaric acid (aq) and water
  5. customThe solvent was evaporated off
  6. dissolutionthe residue was dissolved in 100 ml methanol to which
  7. additionwas added 5 ml water
  8. filtrationThe solid deposit was filtered off
  9. customrecrystallised from ethanol
  10. customto give 3.9 g crude material 1.5 g of this material
  11. stirringThe mixture was stirred at ambient temperature for 2 hours
  12. washThe solid deposit was washed with water
  13. dissolutiondissolved in ether
  14. washthe organic phase washed with tartaric acid(aq)
  15. customThe solvent was evaporated off
  16. customthe residue was evaporated from anhydrous chloroform×2

Sources & evidence

ORD record
ord-d4fab0f23d3944d1862d6944a2d01091
Source dataset
uspto-grants-2004_07
Patent number
US06762175B2

Reaction notes

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