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

HRID 893564노트

반응식

HRID 893564 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-11ded5dc5bf84e10a5c9ac7f08bd70a1
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05126258

반응 노트

불러오는 중…