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

HRID 6334ノート

反応式

HRID 6334 の反応式
[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

参加物

6

反応物 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 4458286Methyl N-Succinimidyl Adipate

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6ee06cc338d74b2ebea19761b8727ee9
出典データセット
uspto-grants-1993_09
特許番号
US05248611

反応ノート

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