Triethylamine → HCID 54224757, compound

HRID 1639263Notes

Reaction equation

HRID 1639263 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].ClC(OCC(C)C)=O.C(N(CC)CC)C.[NH2:30][CH2:31][C:32]([N:34]1[CH2:39][CH2:38][CH:37]([C:40]([NH2:42])=[O:41])[CH2:36][CH2:35]1)=[O:33]>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]([N:34]1[CH2:39][CH2:38][CH:37]([C:40]([NH2:42])=[O:41])[CH2:36][CH2:35]1)=[O:33])=[O:14])=[O:9]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 14672926N-[(2-Oxopyrrolidin-1-yl)acetyl]glycineHCID 19838833HCID 19838833, compound

Product 1

HCID 54224757HCID 54224757, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

8.01 g of N- [(2-oxo-1-pyrrolidinyl)acetyl] glycine was dissolved in 200 ml of dimethylformamide and the solution was cooled to -15° C., to which 5.57 g of isobutyl chloroformate was added and then 4.09 g of triethylamine was added dropwise at -15° to -5° C. This was stirred at -10° to -5° C. for 15 minutes and 7.41 g of 1 glycyl-4-piperidinecarboxamide was added while maintaining the temperature at -10° to -5° C. The reaction liquid was allowed to stand so as to rise its temperature to room temperature over 2 hours. The solid filtered off was suspended in 300 ml of ethanol and the suspension was stirred for 30 minutes and filtered to obtain the solid. This solid was dissolved in the mixture of 20 ml of water and 100 ml of ethanol with heating. The resultant solution was concentrated to 30 ml under atmospheric pressure and 180 ml of ethanol was added followed by allowing to stand to form the precipitate, which was filtered to obtain the titled compound.

Workup

  1. additionwas added
  2. temperaturewhile maintaining the temperature at -10° to -5° C
  3. customThe reaction liquid
  4. customto room temperature
  5. customover 2 hours
  6. filtrationThe solid filtered off
  7. stirringthe suspension was stirred for 30 minutes
  8. filtrationfiltered
  9. customto obtain the solid
  10. temperaturewith heating
  11. concentrationThe resultant solution was concentrated to 30 ml under atmospheric pressure and 180 ml of ethanol
  12. additionwas added
  13. customto form the precipitate, which
  14. filtrationwas filtered

Sources & evidence

ORD record
ord-5690d317065b4b0a857091a7c3688b8c
Source dataset
uspto-grants-1989_11
Patent number
US04883802

Reaction notes

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