Methanol → HCID 14672927, compound

HRID 1638697Notes

Reaction equation

HRID 1638697 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([NH:10][CH2:11][C:12]([OH:14])=O)=[O:9].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:30][CH2:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1)=[O:33].CO>CN(C)C=O.O.C(O)C>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([NH:10][CH2:11][C:12]([NH:30][CH2:31][C:32]([NH:34][C:35]1[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=1)=[O:33])=[O:14])=[O:9]

Participants

8

Reactant 4

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 3614653HCID 3614653, compoundHCID 14672926N-[(2-Oxopyrrolidin-1-yl)acetyl]glycine

Product 1

HCID 14672927HCID 14672927, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

9.01 g of N-[(2-oxo-1-pyrrolidinyl)acetyl]glycine was dissolved in 160 ml of dimethylformamide and the solution was cooled to -13° C., to which 10.32 g of dicyclohexylcarbodiimide dissolved in 15 ml of dimethylformamide was added at -13° to -10° C. After stirring at -10° C. for 30 minutes, 4.53 g of 4-(glycylamino)pyridine was added at -10° to -8° C., which was stirred at -10° to -5° C. for 2 hours and 200 ml of methanol was added while maintaining the temperature at -5° to 0° C. The reaction liquid was allowed to stand so as to rise its temperature to room temperature over 2 hours and then methanol was distilled off under reduced pressure and the precipitated crystal was filtered off. This crystal was extracted with 20 ml of methanol and 100 ml of water, the insoluble matter was filtered off and the filtrate was concentrated to about 15 ml, to which 150 ml of ethanol was added and again the solution was concentrated to about 30 ml, allowed to stand and filterd to obtain 8.1 g of the crude crystal. This was dissolved in 20 ml of water and 200 ml of ethanol with warming and the resultant solution was concentrated to about 40 ml and allowed to stand and the crystal was filterd to obtain the titled compound.

Workup

  1. additionwas added at -13° to -10° C
  2. stirringwhich was stirred at -10° to -5° C. for 2 hours
  3. temperaturewhile maintaining the temperature at -5° to 0° C
  4. customThe reaction liquid
  5. customto room temperature
  6. customover 2 hours
  7. distillationmethanol was distilled off under reduced pressure
  8. filtrationthe precipitated crystal was filtered off
  9. extractionThis crystal was extracted with 20 ml of methanol and 100 ml of water
  10. filtrationthe insoluble matter was filtered off
  11. concentrationthe filtrate was concentrated to about 15 ml, to which 150 ml of ethanol
  12. additionwas added
  13. concentrationagain the solution was concentrated to about 30 ml
  14. customto obtain 8.1 g of the crude crystal
  15. concentrationthe resultant solution was concentrated to about 40 ml

Sources & evidence

ORD record
ord-e59b01421835439d981a20f5aed9cd12
Source dataset
uspto-grants-1989_11
Patent number
US04880819

Reaction notes

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