Dicyclohexylcarbodiimide → HCID 14672911, compound

HRID 1638695Notes

Reaction equation

HRID 1638695 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([OH:10])=O.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:26][CH2:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1)=[O:29]>CN(C)C=O>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([NH:26][CH2:27][C:28]([NH:30][C:31]1[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=1)=[O:29])=[O:10]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 31466872-(2-Oxopyrrolidin-1-yl)acetic acidHCID 3614653HCID 3614653, compound

Product 1

HCID 14672911HCID 14672911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

40.9 g of (2-oxo-1-pyrrolidinyl)acetic acid was dissolved in 300 ml of dimethylformamide and the solution was cooled to 0° C. Then, a solution of 78.7 g of dicylohexylcarbodiimide dissolved in 80 ml of dimethylformamide was added thereto while maintaining the temperature at -2° C. to +1° C. After stirring for 5 minutes, 28.8 g of 4-(glycylamino)pyridine dissolved in 50 ml of dimethylformamide was added while maintaining the temperature at 0° to 3° C. and then the reaction liquid was allowed to stand so as to rise its temperature to room temperature over 2 hours. The liquid was cooled with ice and 200 ml of ice water was added dropwise thereto. The precipitated dicyclohexylurea was filtered off and the solvent was distilled off under reduced pressure. 200 ml of ethanol was added to the residue and stirred and the insoluble matter was filtered off. This insoluble matter was dissolved in 130 ml of water and 50 ml of methanol with warming and then the solution was concentraterd to about 60 ml. After 300 ml of ethanol was added, again the solution was concentrated to about 100 ml and allowed to stand overnight to form the precipitate, which was filtered off to obtain the titled compound.

Workup

  1. additionwas added
  2. temperaturewhile maintaining the temperature at -2° C. to +1° C
  3. additionwas added
  4. temperaturewhile maintaining the temperature at 0° to 3° C.
  5. customthe reaction liquid
  6. customto room temperature
  7. customover 2 hours
  8. additionwas added dropwise
  9. filtrationThe precipitated dicyclohexylurea was filtered off
  10. distillationthe solvent was distilled off under reduced pressure
  11. addition200 ml of ethanol was added to the residue
  12. stirringstirred
  13. filtrationthe insoluble matter was filtered off
  14. dissolutionThis insoluble matter was dissolved in 130 ml of water
  15. temperature50 ml of methanol with warming
  16. additionAfter 300 ml of ethanol was added
  17. concentrationagain the solution was concentrated to about 100 ml
  18. waitto stand overnight
  19. customto form the precipitate, which
  20. filtrationwas filtered off

Sources & evidence

ORD record
ord-a767ffff8bb2464e8a2500d0e6c53d2e
Source dataset
uspto-grants-1989_11
Patent number
US04880819

Reaction notes

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