1-(2-ethoxycarbonylpropanoyl)-L-proline → 1-(2-carboxypropanoyl)-L-proline

HRID 262748Notes

Reaction equation

HRID 262748 reaction equation
C([O:3][C:4]([CH:6]([CH3:17])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])=[O:5])C>[OH-].[Na+].CO>[C:4]([CH:6]([CH3:17])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])([OH:5])=[O:3]

Participants

4

Reactant 1

HCID 536785471-(2-ethoxycarbonylpropanoyl)-L-proline

Product 1

HCID 542987211-(2-carboxypropanoyl)-L-proline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-(2-Ethoxycarbonylpropanoyl)-L-proline (4.1 g.) is dissolved in a mixture of N sodium hydroxide (51 ml.) and methanol (51 ml.). The solution is kept at room temperature for 6 hours and then concentrated to half volume in vacuo. Ion exchange resin (Dowex 50) (50 ml.) is added and the suspension applied to a column of 150 ml. of the same resin. The fractions containing the desired material (carboxyl reagent positive) are pooled and freeze dried to obtain to obtain 1-(2-carboxypropanoyl)-L-proline, yield 1.5 g.

Workup

  1. concentrationconcentrated to half volume in vacuo
  2. additionIon exchange resin (Dowex 50) (50 ml.) is added
  3. additionThe fractions containing the desired material (carboxyl reagent positive)
  4. customfreeze dried
  5. customto obtain

Sources & evidence

ORD record
ord-6d7a0c30f88e4ab78bef8426c1a4a9ba
Source dataset
uspto-grants-1979_05
Patent number
US04154937

Reaction notes

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