Sodium borohydride → HCID 9910284, compound

HRID 618705Notes

Reaction equation

HRID 618705 reaction equation
[O:1]=[C:2]([C:19]1[N:20]=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:22][C:23]=1[CH3:24])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[N:9][CH:10]=1.[BH4-].[Na+].CO.C(Cl)(Cl)Cl>CO>[OH:1][CH:2]([C:19]1[N:20]=[C:21]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[O:22][C:23]=1[CH3:24])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21584188Chloroform methanolHCID 21847959HCID 21847959, compound

Product 1

HCID 9910284HCID 9910284, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 mg (0.47 mmol) of 5-((5-(2-oxo-2-(2-phenyl-5-methyl-4-oxazolyl)ethoxy)-2-pyridyl)methyl)thiazolidin-2,4-dione (Compound No. I-2a-1) was dissolved in 5 ml of methanol dehydrated with molecular sieve. To this solution, was added 21.5 mg of sodium borohydride, and the resultant solution was stirred at room temperature for 1 day. The reaction was terminated with a saturated aqueous solution of ammonium chloride, and the reaction mixture was extracted with chloroform. The reaction product thus obtained was washed with brine, and was dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the solvent was distilled off under a reduced pressure to obtain a residue, and the residue thus obtained was subjected to silica gel column chromatography (eluent: 10%--methanol/chloroform) to obtain 203 mg (quantitative) of pale brown powder of the aimed product (Compound No. I-2a-3).

Workup

  1. customThe reaction was terminated with a saturated aqueous solution of ammonium chloride
  2. extractionthe reaction mixture was extracted with chloroform
  3. customThe reaction product thus obtained
  4. washwas washed with brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customAfter removing the drying agent
  7. filtrationby filtration
  8. distillationthe solvent was distilled off under a reduced pressure
  9. customto obtain a residue
  10. customthe residue thus obtained

Sources & evidence

ORD record
ord-db842186d78549d6a88406b69899a655
Source dataset
uspto-grants-1999_09
Patent number
US05955481

Reaction notes

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