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

HRID 972327Notes

Reaction equation

HRID 972327 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 reaagent positive) are pooled and freeze dried 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 reaagent positive)
  4. customfreeze dried

Sources & evidence

ORD record
ord-ad503935e99547ea87071df09d29d6b8
Source dataset
uspto-grants-1977_10
Patent number
US04052511

Reaction notes

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