Sodium Hydroxide → HCID 42260557, compound

HRID 554114Notes

Reaction equation

HRID 554114 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-d512f9e6480643da93a00f91f073a5ee
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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