1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53248044, compound

HRID 1909349Notes

Reaction equation

HRID 1909349 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][CH:11]([S:15]([OH:18])(=[O:17])=[O:16])[C:12]([OH:14])=[O:13].C(N=C=NCCCN(C)C)C.O[N:31]1[C:35](=[O:36])[CH2:34][CH2:33][C:32]1=[O:37]>CC(N(C)C)=O>[O:37]=[C:32]1[CH2:33][CH2:34][C:35](=[O:36])[N:31]1[O:13][C:12](=[O:14])[CH:11]([S:15]([OH:18])(=[O:16])=[O:17])[CH2:10][CH2:9][S:8][S:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 53248042HCID 53248042, compound

Product 1

HCID 53248044HCID 53248044, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-(pyridin-2-yldisulfanyl)-2-sulfobutanoic acid (245 mg, 0.792 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (345 mg, 2.222 mmol) and 1-hydroxypyrrolidine-2,5-dione (120 mg, 1.043 mmol) were stirred in 8 ml of DMA overnight. The resulting solution was evaporated and the residue was purified on a silica column using MeOH/CH2Cl2 (1:10 to 1:5) containing 0.5% acetic acid as eluting solvent to afford 1-(2,5-dioxopyrrolidin-1-yloxy)-1-oxo-4-(pyridin-2-yldisulfanyl)butane-2-sulfonic acid (258 mg, 0.635 mmol, 80% yield).

Workup

  1. customThe resulting solution was evaporated
  2. customthe residue was purified on a silica column
  3. additioncontaining 0.5% acetic acid
  4. washas eluting solvent

Sources & evidence

ORD record
ord-824a94d983214a8c88aceca2c6dbf45a
Source dataset
uspto-grants-2013_12
Patent number
US08598362B2

Reaction notes

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