Dicyclohexylcarbodiimide → 2,2-Dimethyl-1-[2-(4-hydroxy-2-oxo-1-pyrrolidineacetamido)acetyl]-4-imidazolidinone

HRID 256367Notes

Reaction equation

HRID 256367 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]([N:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1([CH3:23])[CH3:22])=[O:15].C1CCC(N=C=NC2CCCCC2)CC1>CS(C)=O.O1CCCC1.O>[CH3:22][C:17]1([CH3:23])[NH:18][C:19](=[O:21])[CH2:20][N:16]1[C:14](=[O:15])[CH2:13][NH:12][C:8](=[O:10])[CH2:7][N:5]1[CH2:6][CH:2]([OH:1])[CH2:3][C:4]1=[O:11]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 111265411-Pyrrolidineacetic acid, 4-hydroxy-2-oxo-, (+-)-HCID 201637131-(2-Aminoacetyl)-2,2-dimethyl-4-imidazolidinone

Product 1

HCID 544350872,2-Dimethyl-1-[2-(4-hydroxy-2-oxo-1-pyrrolidineacetamido)acetyl]-4-imidazolidinoneYield 21.9%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into an ice cold solution of 4-hydroxy-2-oxo-1-pyrrolidineacetic acid (0.95 g) and 1-(2-aminoacetyl)-2,2-dimethyl-4-imidazolidinone (1 g) in dimethylsulfoxide (30 ml) a solution of DCC (1,22 g) in tetrahydrofuran (10 ml) was added dropwise. The solution was stirred at room temperature overnight and then heated at 50° for 4 hours. After cooling the solution was diluted with water and the resulting precipitate was filtered off. The filtrate was evaporated to dryness under vacuum. The residue was dissolved in water and eluted on a column of Amberlite IR 120H (20 ml). The eluate was treated with Amberlite IRA 68 (10 ml), filtered and evaporated under vacuum. The residue was triturated with isopropanol to yield 0.4 g of the title compound, m.p. 227°-229° .

Workup

  1. temperatureheated at 50° for 4 hours
  2. temperatureAfter cooling the solution
  3. filtrationthe resulting precipitate was filtered off
  4. customThe filtrate was evaporated to dryness under vacuum
  5. dissolutionThe residue was dissolved in water
  6. washeluted on a column of Amberlite IR 120H (20 ml)
  7. additionThe eluate was treated with Amberlite IRA 68 (10 ml)
  8. filtrationfiltered
  9. customevaporated under vacuum
  10. customThe residue was triturated with isopropanol

Sources & evidence

ORD record
ord-3c6d88fb788c483799df28de6c388000
Source dataset
uspto-grants-1987_10
Patent number
US04703054

Reaction notes

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