Dicyclohexylcarbodiimide → 1-({[(Pyrimidin-2-yl)sulfanyl]acetyl}oxy)pyrrolidine-2,5-dione

HRID 570090Notes

Reaction equation

HRID 570090 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].C1(N=C=NC2CCCCC2)CCCCC1.[N:24]1[CH:29]=[CH:28][CH:27]=[N:26][C:25]=1[S:30][CH2:31][C:32](O)=[O:33]>CN(C=O)C>[O:8]=[C:3]1[CH2:4][CH2:5][C:6](=[O:7])[N:2]1[O:1][C:32](=[O:33])[CH2:31][S:30][C:25]1[N:26]=[CH:27][CH:28]=[CH:29][N:24]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 581022(Pyrimidin-2-ylthio)acetic acid

Product 1

HCID 594044951-({[(Pyrimidin-2-yl)sulfanyl]acetyl}oxy)pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.31 g (107 mMol) N-hydroxysuccinimide and 22.70 g (110 mMol) dicyclohexylcarbodiimide were added at −35° C. to a solution of 18.27 g (107 mMol) (Pyrimidin-2-ylsulfanyl)-acetic acid (a) dissolved in 200 ml DMF. The reaction mixture was stirred for 16 h under argon. The residue was filtered and the filtrate was evaporated in vacuo to dryness. The remaining product was dissolved under reflux in 400 ml ethyl acetate, the hot solution was filtered and the mixture was subjected to a chromatographic purification (Florisil) using ethyl acetate. The compound was then recrystallised from ethyl acetate.

Workup

  1. filtrationThe residue was filtered
  2. customthe filtrate was evaporated in vacuo to dryness
  3. dissolutionThe remaining product was dissolved
  4. temperatureunder reflux in 400 ml ethyl acetate
  5. filtrationthe hot solution was filtered
  6. customthe mixture was subjected to a chromatographic purification (Florisil)
  7. customThe compound was then recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-445e9cfb716949de991987b91306f145
Source dataset
uspto-grants-2015_05
Patent number
US09023656B2

Reaction notes

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