Sodium Hydroxide → HCID 42260557, compound

HRID 2238520Notes

Reaction equation

HRID 2238520 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C@H:5]([C:13]([O:15]C)=[O:14])[CH2:4][CH2:3]1.[OH-].[Na+]>C(O)C>[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C@H:5]([C:13]([OH:15])=[O:14])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 42260998Methyl 5-oxo-1-phenylprolinate

Product 1

HCID 42260557HCID 42260557, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 5-oxo-1-phenylprolinate (0.078 g, 0.36 mmol) was combined with 2N aqueous sodium hydroxide (2 ml) in ethanol (2 ml) at 0° C. The mixture was stirred at between −10° C. and 0° C. for 5 hours. The solvent was then evaporated in vacuo and the residue was acidified to pH1 by the addition of 2M aqueous hydrogen chloride. To this was added dichloromethane and the mixture was passed through a phase separator. The aqueous layer was washed with more dichloromethane and then the combined dichloromethane layers were evaporated to give 5-oxo-1-phenyl-proline (0.072 g) as a yellow gum which was used without further purification in the next step.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. additionthe residue was acidified to pH1 by the addition of 2M aqueous hydrogen chloride
  3. additionTo this was added dichloromethane
  4. washThe aqueous layer was washed with more dichloromethane
  5. customthe combined dichloromethane layers were evaporated

Sources & evidence

ORD record
ord-66641b8a9b1f45db94ce00544d9348cc
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

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