Acetic Acid → HCID 57787153, compound

HRID 2426784Notes

Reaction equation

HRID 2426784 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.C([O:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH:36]=O)[CH:31]=2)=[C:25]([CH3:38])[CH:24]=1)(=O)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+:56]>O.C1COCC1>[OH:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][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:31]=2)=[C:25]([CH3:38])[CH:24]=1.[Na+:56]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 18624553HCID 18624553, compoundHCID 57787266HCID 57787266, compound

Product 1

HCID 57787153HCID 57787153, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-aminobenzyl)-1,2,4-oxadiazolidine-3,5-dione (365 mg), 2-[(3′-formyl-2,6-dimethylbiphenyl-4-yl)oxy]ethyl acetate (660 mg), acetic acid (0.3 ml), THF (20 ml) and Molecular Sieves 4A (1 g) was stirred at room temperature for 22 hours. Sodium triacetoxyborohydride (560 mg) was added to the reaction mixture, followed by stirring at room temperature for 22 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, toluene was added to the residue, the solvent was again evaporated under a reduced pressure, and then the residue was purified by silica gel column chromatography (hexane-ethyl acetate). Methanol (10 ml) and sodium methoxide (52 mg) were added to the resulting pale yellow foamy substance (406 mg), followed by stirring for 2 hours while heating at 60° C. The solvent was evaporated under a reduced pressure, and chloroform was added to the residue, followed by washing with water and a saturated sodium chloride aqueous solution and drying over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and THF (5 ml), methanol (5 ml) and a 1 M sodium hydroxide aqueous solution (0.81 ml) were added to the resulting pale yellow foamy substance (373 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), the resulting pale yellow foamy substance was 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′-(2-hydroxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methyl}amino)benzyl]-3,5-dioxo-1,2,4-oxadiazolidin-4-ide (226 mg) as a pale yellow solid.

Workup

  1. stirringby stirring at room temperature for 22 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under a reduced pressure, toluene
  6. additionwas added to the residue
  7. customthe solvent was again evaporated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  9. additionMethanol (10 ml) and sodium methoxide (52 mg) were added to the resulting pale yellow foamy substance (406 mg)
  10. stirringby stirring for 2 hours
  11. temperaturewhile heating at 60° C
  12. customThe solvent was evaporated under a reduced pressure, and chloroform
  13. additionwas added to the residue
  14. washby washing with water
  15. dry with materiala saturated sodium chloride aqueous solution and drying over anhydrous magnesium sulfate
  16. customThe solvent was evaporated under a reduced pressure, and THF (5 ml), methanol (5 ml)
  17. additiona 1 M sodium hydroxide aqueous solution (0.81 ml) were added to the resulting pale yellow foamy substance (373 mg)
  18. stirringby stirring at room temperature for 5 minutes
  19. customThe solvent was evaporated under a reduced pressure
  20. customthe residue was purified by an ODS column chromatography (water-acetonitrile)
  21. additionby adding diethyl ether
  22. filtrationThe solid was collected by filtration
  23. customdried
  24. temperatureby heating under a reduced pressure

Sources & evidence

ORD record
ord-e134c4f0d3274b1eab9b3cc633312648
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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