Hydrochloric Acid → 5-(2,4-Dimethoxybenzyl)-4-oxo-5-azaspiro[2.4]heptane-7-carboxylic Acid

HRID 83584Notes

Reaction equation

HRID 83584 reaction equation
C[O:2][C:3]([CH:5]1[C:9]2([CH2:11][CH2:10]2)[C:8](=[O:12])[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])[CH2:6]1)=[O:4].[OH-].[Na+].Cl>CCCCCC.C(OCC)(=O)C>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:13][N:7]1[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[C:9]2([CH2:11][CH2:10]2)[C:8]1=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71287769HCID 71287769, compound

Product 1

HCID 866803935-(2,4-Dimethoxybenzyl)-4-oxo-5-azaspiro[2.4]heptane-7-carboxylic AcidYield 82.3%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 5-(2,4-dimethoxybenzyl)-4-oxo-5-azaspiro[2.4]heptane-7-carboxylic acid methyl ester (2.02 g) in tetrahydrofuran/methanol (1/1, 12 ml) was added a 1M aqueous solution of sodium hydroxide (12 ml) at room temperature, and the mixture was stirred for 1 hour. To this reaction solution was added a 2M aqueous solution of hydrochloric acid (6 ml), and the mixture was stirred, and then concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate, the solution was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. To the resulting solid was added diisopropyl ether (8 ml), and the mixture was stirred. A solid was collected from this suspension by filtration, and was dried under reduced pressure to give the titled compound (1.59 g).

Workup

  1. stirringthe mixture was stirred
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washthe solution was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the resulting solid was added diisopropyl ether (8 ml)
  8. stirringthe mixture was stirred
  9. filtrationA solid was collected from this suspension by filtration
  10. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-829fed76691b496cad1ae5ad748266b4
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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