Fumaric Acid → HCID 10006016, compound

HRID 1458529Notes

Reaction equation

HRID 1458529 reaction equation
[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[N:10]([CH:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>C(O)C>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[N:10]([CH:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 9886185HCID 9886185, compound

Product 1

HCID 10006016HCID 10006016, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Benzyl-3-(3-morpholino-1-phenylpropyl)-1,3-oxazolidin-2-one (diastereomer A) (376 mg, 1.0 mmol) prepared in Example 1 was dissolved in ethanol (5 ml). To the solution, fumaric acid (115 mg, 1.0 mmol) was added and dissolved under heating. From the resulting solution, ethanol was removed by distillation under reduced pressure, and then the residue was crystallized from ethanol/hexane (3/1). The obtained crystalline product was collected by filtration, washed with ethanol/hexane (3/1), and dried under reduced pressure overnight at room temperature to give 234 mg of the titled compound as a white crystalline powder (yield: 46%).

Workup

  1. dissolutiondissolved
  2. temperatureunder heating
  3. customFrom the resulting solution, ethanol was removed by distillation under reduced pressure
  4. customthe residue was crystallized from ethanol/hexane (3/1)
  5. filtrationThe obtained crystalline product was collected by filtration
  6. washwashed with ethanol/hexane (3/1)
  7. customdried under reduced pressure overnight at room temperature

Sources & evidence

ORD record
ord-894e31d742be48cfad13d3cda21523f3
Source dataset
uspto-grants-1998_12
Patent number
US05852006

Reaction notes

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