Dicyclohexylcarbodiimide → HCID 14772799, compound

HRID 1885406Notes

Reaction equation

HRID 1885406 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:11][CH:10]([C:12]([OH:14])=O)[CH2:9][S:8]2)[CH:2]=1.[N:15]1([C:20]([CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:11][CH:10]([C:12]([N:26]3[CH2:25][CH2:24][N:23]([CH2:22][C:20]([N:15]4[CH2:16][CH2:17][CH2:18][CH2:19]4)=[O:21])[CH2:28][CH2:27]3)=[O:14])[CH2:9][S:8]2)[CH:2]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1006141-((Pyrrolidine-1-carbonyl)methyl)piperazineHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acid

Product 1

HCID 14772799HCID 14772799, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-pyridyl)thiazolidine-4-caroxylic acid 2.1 g, 1-(pyrrolidinecarbonylmethyl)piperazine 1.8 g, 1-hydroxybenzotriazole 1.5 g and N,N-dimethylformamide 50 ml was added dicyclohexylcarbodiimide 2 g under ice-cooling, and the mixture was stirred overnight at room temperature. The resultant dicyclohexylurea was filtered off and the filtrate concentrated under reduced pressure. To the residue were added ethyl acetate 100 ml and water 10 ml, the mixture was basified by addition of sodium carbonate, sodium chloride added until saturation and allowed to stand. The organic layer was separated, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with a mixture solution of ethyl acetate -methanol (6:4) to give 2.1 g of 1-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]-4-[1-(pyrrolidinyl)carbonylmethyl]piperazine.

Workup

  1. temperaturecooling
  2. filtrationThe resultant dicyclohexylurea was filtered off
  3. concentrationthe filtrate concentrated under reduced pressure
  4. additionTo the residue were added ethyl acetate 100 ml and water 10 ml
  5. additionthe mixture was basified by addition of sodium carbonate, sodium chloride
  6. additionadded until saturation
  7. customThe organic layer was separated
  8. washwashed with saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washeluted with a mixture solution of ethyl acetate -methanol (6:4)

Sources & evidence

ORD record
ord-108450279efa49d9989f03225016eb81
Source dataset
uspto-grants-1992_09
Patent number
US05144035

Reaction notes

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