Sodium triacetoxyborohydride → HCID 57787096, compound

HRID 2426785Notes

Reaction equation

HRID 2426785 reaction equation
C([O:4][C:5]([CH3:26])([CH3:25])[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=O)[C:16]=2[CH3:23])=[C:11]([CH3:24])[CH:10]=1)(=O)C.[NH2:27][C:28]1[CH:41]=[CH:40][C:31]([CH2:32][N:33]2[C:37](=[O:38])[NH:36][C:35](=[O:39])[O:34]2)=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+:55]>C(O)(=O)C>[OH:4][C:5]([CH3:26])([CH3:25])[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:27][C:28]3[CH:41]=[CH:40][C:31]([CH2:32][N:33]4[C:37](=[O:38])[N-:36][C:35](=[O:39])[O:34]4)=[CH:30][CH:29]=3)[C:16]=2[CH3:23])=[C:11]([CH3:24])[CH:10]=1.[Na+:55]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 18624553HCID 18624553, compoundHCID 57787801HCID 57787801, compound

Product 1

HCID 57787096HCID 57787096, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-[(3′-formyl-2,2′-dimethylbiphenyl-4-yl)oxy]-1,1-dimethylpropyl acetate (479 mg), 2-(4-aminobenzyl)-1,2,4-oxadiazolidine-3,5-dione (340 mg) and acetic acid (6 ml) was stirred at room temperature for 20 hours. Sodium triacetoxyborohydride (573 mg) was added to the reaction solution, followed by stirring at room temperature for 2 hours. After evaporation of the solvent under a reduced pressure, water was added to the residue, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate), and a mixture of the resulting pale yellow foamy substance (719 mg), THF (5 ml), methanol (5 ml) and a 1 M sodium hydroxide aqueous solution (4 ml) was stirred at 50° C. for 4 hours. The pH was made to 4 to 5 by adding 1 M hydrochloric acid, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate), and a 1 M sodium hydroxide aqueous solution (0.89 ml) was added to a mixture of the resulting pale yellow oil (448 mg), THF (3 ml) and methanol (3 ml), followed by stirring for 10 minutes. After evaporation of the solvent under a reduced pressure, the resulting residue was washed with diethyl ether to obtain sodium 2-[4-({[4′-(3-hydroxy-3-methylbutoxy)-2,2′-dimethylbiphenyl-3-yl]methyl}amino)benzyl]-3,5-dioxo-1,2,4-oxadiazolidin-4-ide (398 mg) as a white solid.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. customAfter evaporation of the solvent under a reduced pressure, water
  3. additionwas added to the residue
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  8. additiona mixture of the resulting pale yellow foamy substance (719 mg), THF (5 ml), methanol (5 ml)
  9. stirringa 1 M sodium hydroxide aqueous solution (4 ml) was stirred at 50° C. for 4 hours
  10. additionby adding 1 M hydrochloric acid
  11. extractionfollowed by extraction with chloroform
  12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  13. customthe solvent was evaporated under a reduced pressure
  14. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  15. additiona 1 M sodium hydroxide aqueous solution (0.89 ml) was added to a mixture of the resulting pale yellow oil (448 mg), THF (3 ml) and methanol (3 ml)
  16. stirringby stirring for 10 minutes
  17. customAfter evaporation of the solvent under a reduced pressure
  18. washthe resulting residue was washed with diethyl ether

Sources & evidence

ORD record
ord-cb987fd94b4f41f081f6f9504b4e3fd5
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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