Sodium Hydroxide → HCID 42260557, compound

HRID 2238481Notes

Reaction equation

HRID 2238481 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+]>CO>[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 91.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-oxo-1-phenylprolinate (0.054 g, 0.25 mmol) was combined with 2M aqueous sodium hydroxide (0.160 ml, 0.32 mmol) in methanol (1 ml) and stirred overnight at room temperature. The solvent was then evaporated and the residue taken up in ethyl acetate and washed with 2M aqueous hydrogen chloride. The aqueous layer was separated and washed twice more with ethyl acetate and then the combined ethyl acetate layers were dried using a phase separator and evaporated to give 5-oxo-1-phenyl-proline (0.047 g) as a clear oil.

Workup

  1. customThe solvent was then evaporated
  2. washwashed with 2M aqueous hydrogen chloride
  3. customThe aqueous layer was separated
  4. washwashed twice more with ethyl acetate
  5. dry with materialthe combined ethyl acetate layers were dried
  6. customevaporated

Sources & evidence

ORD record
ord-ea3cf6cd2f6841ff9f3315047c000092
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

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