Itaconic acid → HCID 10421488, compound

HRID 344228Notes

Reaction equation

HRID 344228 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5](O)=[O:6])=[CH2:3].[C:10]1([C@@H:16]([NH2:18])[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>CN1CCN(C)C1=O>[C:10]1([C@@H:16]([N:18]2[C:5](=[O:6])[CH2:4][CH:2]([C:1]([OH:9])=[O:8])[CH2:3]2)[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 811Itaconic acidHCID 962WaterHCID 758181-Phenethylamine, (-)-

Product 1

HCID 10421488HCID 10421488, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
80 °C

Procedure

Itaconic acid (650 g) and (S)-1-phenylethylamine (605 g) were suspended in 1,3-dimethylimidazolidinone (650 ml), and the suspension was stirred at 80° C. for 1 hr with heating, and further at 120° C. for 3 hr with heating. The mixture was cooled to room temperature, and water (4 l) was added. The precipitated crystals were collected by filtration and dried to give 950 g of 1-((S)-1-phenylethyl)-5-oxo-3-pyrrolidinecarboxylic acid. The crystals were recrystallized 3 times with isopropyl alcohol to give 156 g of (3S)-1-((S)-1-phenylethyl)-5-oxo-3-pyrrolidinecarboxylic acid.

Workup

  1. temperaturewith heating
  2. temperaturefurther at 120° C. for 3 hr with heating
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationThe precipitated crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-0d508d26be89471f8089d2a4c7b2c373
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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