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

HRID 1909346Notes

Reaction equation

HRID 1909346 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].O[N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].C(N=C=NCCCN(C)C)C>CC(N(C)C)=O>[O:26]=[C:21]1[CH2:22][CH2:23][C:24](=[O:25])[N:20]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)carbodiimide2×HCID 80170N-HydroxysuccinimideHCID 53248042HCID 53248042, compound

Product 1

HCID 53248044HCID 53248044, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-(pyridin-2-yldisulfanyl)-2-sulfobutanoic acid (0.292 mg, 0.944 μmol) in DMA (8 mL) was added 1-hydroxypyrrolidine-2,5-dione (0.120 mg, 1.043 μmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (EDC, 0.647 mg, 4.17 μmol. The reaction mixture was stirred overnight, evaporated and purified on a SiO2 cartridge (40 g) eluting with a mixture of Acetone/DCM/HOAc (4:1:0.01). Product containing fractions were pooled, evaporated and solidified with EtOH/Tol/Hexane to afford 1-(2,5-dioxopyrrolidin-1-yloxy)-1-oxo-4-(pyridin-2-yldisulfanyl)butane-2-sulfonic acid (sulfo-SPDB, 0.270 mg, 0.664 μmol, 70.4% yield).

Workup

  1. customevaporated
  2. custompurified on a SiO2 cartridge (40 g)
  3. washeluting with a mixture of Acetone/DCM/HOAc (4:1:0.01)
  4. additionProduct containing fractions
  5. customevaporated

Sources & evidence

ORD record
ord-3fbe8363fa974f9580ac770b77264d7e
Source dataset
uspto-grants-2013_12
Patent number
US08598362B2

Reaction notes

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