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

HRID 65713Notes

Reaction equation

HRID 65713 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-8448bd16a15c41d0a037a2d38a5457f8
Source dataset
uspto-grants-1978_12
Patent number
US04128653

Reaction notes

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