Isocyanate → 2-{(E)-4-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-but-3-enyl}-isoindole-1,3-dione

HRID 660590

反応式

HRID 660590 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N-]=C=O.[CH2:22]([O:29][C:30]1[CH:31]=[C:32](/[CH:50]=[CH:51]/[CH2:52][CH2:53][N:54]2[C:62](=[O:63])[C:61]3[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=3)[C:55]2=[O:64])[CH:33]=[CH:34][C:35]=1[N:36]1[CH2:40][C:39](=[O:41])[N:38](CC[Si](C)(C)C)[S:37]1(=[O:49])=[O:48])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([O:29][C:30]1[CH:31]=[C:32](/[CH:50]=[CH:51]/[CH2:52][CH2:53][N:54]2[C:55](=[O:64])[C:56]3[C:61](=[CH:60][CH:59]=[CH:58][CH:57]=3)[C:62]2=[O:63])[CH:33]=[CH:34][C:35]=1[N:36]1[CH2:40][C:39](=[O:41])[NH:38][S:37]1(=[O:48])=[O:49])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 105034IsocyanateHCID 2724141Tetrabutylammonium FluorideHCID 688387512-((E)-4-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-but-3-enyl)-isoindole-1,3-dione

生成物 1

HCID 688427202-{(E)-4-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-but-3-enyl}-isoindole-1,3-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Tetrabutylammonium fluoride (1.0M in THF, 1.5 mL) is added to a suspension of PS-isocyanate resin (0.4 g) in THF (1.5 mL) and the mixture is stirred at RT for 2 h. The resin is filtered off and the filtrate is added to a solution of 2-((E)-4-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-but-3-enyl)-isoindole-1,3-dione (90 mg, 0.146 mmol) in THF (1 mL). The reaction is stirred at 65° C. for 1 h and at RT for 18 h. The mixture is cooled and concentrated. The residue is partitioned between EtOAc and water and the organic layer is washed with 2N HCl (3×) and saturated aqueous sodium chloride. The organic layer is dried over Na2SO4 and the solvent removed under reduced pressure to give the title compound: (M−1)−=516.

後処理

  1. filtrationThe resin is filtered off
  2. stirringThe reaction is stirred at 65° C. for 1 h and at RT for 18 h
  3. temperatureThe mixture is cooled
  4. concentrationconcentrated
  5. customThe residue is partitioned between EtOAc and water
  6. washthe organic layer is washed with 2N HCl (3×) and saturated aqueous sodium chloride
  7. dry with materialThe organic layer is dried over Na2SO4
  8. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-7c52c8f1e9b640c7b4ae547d76b47424
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

関連ノート

読み込み中…