Acetic Acid → HCID 57787267, compound

HRID 2426783Notes

Reaction equation

HRID 2426783 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[C:11](=[O:12])[NH:10][C:9](=[O:13])[O:8]2)=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=O)[CH:24]=2)=[C:19]([CH3:31])[CH:18]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+:49]>C1COCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][NH:1][C:2]3[CH:15]=[CH:14][C:5]([CH2:6][N:7]4[C:11](=[O:12])[N-:10][C:9](=[O:13])[O:8]4)=[CH:4][CH:3]=3)[CH:24]=2)=[C:19]([CH3:31])[CH:18]=1.[Na+:49]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 18624553HCID 18624553, compoundHCID 86632832HCID 86632832, compound

Product 1

HCID 57787267HCID 57787267, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-aminobenzyl)-1,2,4-oxadiazolidine-3,5-dione (500 mg), 4′-chloro-2′-methylbiphenyl-3-carbaldehyde (668 mg), acetic acid (0.33 ml) and THF (40 ml) was stirred at room temperature for 24 hours. Sodium triacetoxyborohydride (767 mg) was added to the reaction mixture, followed by stirring at room temperature for 15 minutes. The solvent was evaporated under a reduced pressure, and water was added to the residue, followed by extraction with chloroform. The organic layer was washed with a saturated sodium chloride aqueous solution, the solvent was evaporated under a reduced pressure, toluene was added to the residue, and the solvent was again evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), and THF (5 ml), methanol (5 ml) and a 1 M sodium hydroxide aqueous solution (1.47 ml) were added to the resulting pale yellow foamy substance (620 mg), followed by stirring at room temperature for 5 minutes. The solvent was evaporated under a reduced pressure, the residue was purified by an ODS column chromatography (water-acetonitrile) and made into a solid by adding diethyl ether. The solid was collected by filtration and then dried by heating under a reduced pressure to obtain sodium 2-(4-{[(4′-chloro-2′-methylbiphenyl-3-yl)methyl]amino}benzyl)3,5-dioxo-1,2,4-oxadiazolidin-4-ide (160 mg) as a white solid.

Workup

  1. stirringby stirring at room temperature for 15 minutes
  2. customThe solvent was evaporated under a reduced pressure, and water
  3. additionwas added to the residue
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. customthe solvent was evaporated under a reduced pressure, toluene
  7. additionwas added to the residue
  8. customthe solvent was again evaporated under a reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate), and THF (5 ml), methanol (5 ml)
  10. additiona 1 M sodium hydroxide aqueous solution (1.47 ml) were added to the resulting pale yellow foamy substance (620 mg)
  11. stirringby stirring at room temperature for 5 minutes
  12. customThe solvent was evaporated under a reduced pressure
  13. customthe residue was purified by an ODS column chromatography (water-acetonitrile)
  14. additionby adding diethyl ether
  15. filtrationThe solid was collected by filtration
  16. customdried
  17. temperatureby heating under a reduced pressure

Sources & evidence

ORD record
ord-0946fa90aa494d8bb1395948e2aa8310
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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