Acetic Acid → HCID 66600719, compound

HRID 1621726Notes

Reaction equation

HRID 1621726 reaction equation
C([N:14]1[CH2:17][C:16]2([C:21](=[O:22])[NH:20][C:19](=[O:23])[NH:18]2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:24]([OH:27])(=[O:26])[CH3:25].[H][H]>[Pd].CO.C(OCC)C>[C:24]([OH:27])(=[O:26])[CH3:25].[CH2:15]1[C:16]2([C:21](=[O:22])[NH:20][C:19](=[O:23])[NH:18]2)[CH2:17][NH:14]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 66599950HCID 66599950, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66600719HCID 66600719, compoundYield 69.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-benzhydryl-2,5,7-triazaspiro[3.4]octane-6,8-dione (0.258 g, 0.839 mmol) and 10% palladium on carbon (0.179 g, 0.168 mmol) in 4 mL MeOH was treated with acetic acid (0.0961 mL, 1.68 mmol) and the slurry was stirred under a balloon containing hydrogen overnight. The reaction was filtered, rinsed with MeOH, and concentrated in vacuo to give an oil. Concentration from benzene gave a solid which was suspended in diethylether, sonicated, filtered, and dried in vacuo to give 2,5,7-triazaspiro[3.4]octane-6,8-dione acetate (0.117 g, 69.3% yield) as a white solid.

Workup

  1. filtrationThe reaction was filtered
  2. washrinsed with MeOH
  3. concentrationconcentrated in vacuo
  4. customto give an oil
  5. concentrationConcentration from benzene
  6. customgave a solid which
  7. customsonicated
  8. filtrationfiltered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-918ac6e978224eeca823bb1489cfa256
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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