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

HRID 65720Notes

Reaction equation

HRID 65720 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-46e5eb741c8c431fa40ca721433c5e1f
Source dataset
uspto-grants-1978_12
Patent number
US04128653

Reaction notes

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