Triacetoxyperiodinane → HCID 89657403、化合物

HRID 930913ノート

反応式

HRID 930913 の反応式
[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[C:16]2[CH:25]=[C:24]([CH2:26][OH:27])[NH:23][C:17]=2[C:18](=[O:22])[N:19]([CH3:21])[CH:20]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.S(=O)(O)[O-].[Na+]>ClCCl.C(=O)(O)[O-].[Na+]>[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:12])=[O:13])=[CH:7][C:6]=1[C:15]1[C:16]2[CH:25]=[C:24]([CH:26]=[O:27])[NH:23][C:17]=2[C:18](=[O:22])[N:19]([CH3:21])[CH:20]=1

参加物

6

反応物 3

HCID 159087TriacetoxyperiodinaneHCID 23665763Sodium BisulfiteHCID 89656277HCID 89656277、化合物

生成物 1

HCID 89657403HCID 89657403、化合物収率 79.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

To the solution of Example 276 (1.0 g, 2.2 mmol) in dichloromethane (50 mL) at 0° C. was added Dess-MartinPeriodinane (1.84 g, 4.34 mmol) and the reaction mixture was stirred at 0° C. for 30 minutes. The reaction mixture was then stirred at ambient temperature for three hours. A solution of sodium bisulfite (0.9 g, 9 mmol) in saturated aqueous sodium bicarbonate (5 mL) was added, and the reaction mixture was stirred for 15 minutes and extracted with ethyl acetate. The organic layer was dried (anhydrous sodium sulfate), filtered, and concentrated to provide the title compound (0.80 g, 70% yield).

後処理

  1. stirringThe reaction mixture was then stirred at ambient temperature for three hours
  2. stirringthe reaction mixture was stirred for 15 minutes
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-20c0c9099b114426b94205ba42f96c0b
出典データセット
uspto-grants-2016_03
特許番号
US09296741B2

反応ノート

読み込み中…