Dicyclohexylcarbodiimide → N-(2-Amino-2-oxoethyl)-2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetamide

HRID 1608019Notes

Reaction equation

HRID 1608019 reaction equation
[OH:1][CH:2]1[CH2:6][N:5]([CH2:7][C:8]([OH:10])=O)[C:4](=[O:11])[CH2:3]1.[NH2:12][CH2:13][C:14]([NH2:16])=[O:15].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[OH:1][CH:2]1[CH2:6][N:5]([CH2:7][C:8]([NH:12][CH2:13][C:14]([NH2:16])=[O:15])=[O:10])[C:4](=[O:11])[CH2:3]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 69020GlycinamideHCID 111265411-Pyrrolidineacetic acid, 4-hydroxy-2-oxo-, (+-)-

Product 1

HCID 11701304N-(2-Amino-2-oxoethyl)-2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetamideYield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cold mixture of 4-hydroxy-2-oxo-1-pyrrolidineacetic acid (1 g) and glycinamide (700 mg) in dimethylformamide (20 ml), dicyclohexylcarbodiimide (1.3 g) was added at once. Stirring was continued for 5 hours at room temperature, then the solvent was removed under vacuum. The residue was suspended in water (20 ml) and stirred for 30 minutes at room temperature. The insoluble material was filtered off and the filtrate evaporated to dryness. The residue was triturated with 2-propanol to yield the title compound (700 mg).

Workup

  1. additionwas added at once
  2. customthe solvent was removed under vacuum
  3. stirringstirred for 30 minutes at room temperature
  4. filtrationThe insoluble material was filtered off
  5. customthe filtrate evaporated to dryness
  6. customThe residue was triturated with 2-propanol

Sources & evidence

ORD record
ord-97cc25a20fc246338129318564fa2f87
Source dataset
uspto-grants-1989_09
Patent number
US04868313

Reaction notes

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