Succinic anhydride → (2S)-2-Carboxy-gamma-oxo-1-pyrrolidinebutanoic acid

HRID 972334Notes

Reaction equation

HRID 972334 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[NH:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11]>C(O)(=O)C>[C:4]([CH2:3][CH2:2][C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 145742L-Proline

Product 1

HCID 194156(2S)-2-Carboxy-gamma-oxo-1-pyrrolidinebutanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Succinic anhydride (67 mmoles, 6.7 g.) is dissolved in 100 ml. of hot glacial acetic acid and cooled to room temperature. To this, while stirring (67 mmoles, 7.7 g.) L-proline is added. After 20 hours at room temperature, the reaction mixture is concentrated to dryness in vacuo. The residue is extracted three times with hot ethyl acetate and cooled to room temperature. To the pooled extracts containing the 1-(3-carboxypropanoyl)-L-proline, dicyclohexylamine is added and crystals form which are recrystallized from hot isopropanol, yield 11.3 g. The dicyclohexylamine salt has m.p. (170) 175°-177°.

Workup

  1. additionis added
  2. concentrationthe reaction mixture is concentrated to dryness in vacuo
  3. extractionThe residue is extracted three times with hot ethyl acetate
  4. additionTo the pooled extracts containing the 1-(3-carboxypropanoyl)-L-proline, dicyclohexylamine
  5. additionis added
  6. customcrystals form which are recrystallized from hot isopropanol, yield 11.3 g
  7. custom(170) 175°-177°

Sources & evidence

ORD record
ord-e43fca40cf8c43559cd82e5416aad418
Source dataset
uspto-grants-1977_10
Patent number
US04052511

Reaction notes

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