Sodium Iodide → 6-((2,5-Dioxopyrrolidin-1-yl)oxy)-6-oxohexanoic acid

HRID 2081954Notes

Reaction equation

HRID 2081954 reaction equation
[C:1]([O:17]C)(=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15])=[O:7].Cl[Si](C)(C)C.[I-].[Na+]>C(#N)C.C(OCC)(=O)C>[C:10]1(=[O:15])[N:9]([O:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:17])=[O:16])[C:13](=[O:14])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 4458286Methyl 6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexanoate

Product 1

HCID 120522896-((2,5-Dioxopyrrolidin-1-yl)oxy)-6-oxohexanoic acidYield 75.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl succinimidyl adipate (4.5 g, 17.5 mmol), chlorotrimethylsilane (11.1 ml, 87.5 mmol) and sodium iodide (13.1 g, 87.5 mmol) in 10 ml of acetonitrile was heated at reflux for 12 hours. The mixture was then cooled to room temperature and diluted with ethyl acetate. The reaction mixture was washed repeatedly with 5 percent aqueous sodium bisulfite until the organic solution was colorless. Then it was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to provide 3.2 g (71 percent yield by weight) of adipic acid monosuccinimidyl ester as a white solid.

Workup

  1. temperatureat reflux for 12 hours
  2. washThe reaction mixture was washed repeatedly with 5 percent aqueous sodium bisulfite until the organic solution
  3. washThen it was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f655c6ba110436886cd9e450e375530
Source dataset
uspto-grants-1993_02
Patent number
US05187086

Reaction notes

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