ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

tert-Butylsulfinamide, (S)-(-)- → (NE,S)-2-methyl-N-[2,2,2-trifluoro-1-[4-(6,6,6-trifluorohexoxy)phenyl]ethylidene]propane-2-sulfinamide

HRID 1629767
ノート
印刷プレビュー

反応式

HRID 1629767 の反応式
[F:1][C:2]([F:22])([F:21])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:7][CH:6]=1)=O.[CH3:23][C:24]([S@@:27]([NH2:29])=[O:28])([CH3:26])[CH3:25]>C1COCC1.CCCCCC.CCOC(C)=O.C(O[Ti](OCC)(OCC)OCC)C>[CH3:23][C:24]([S@@:27](/[N:29]=[C:3](\[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:7][CH:6]=1)/[C:2]([F:22])([F:21])[F:1])=[O:28])([CH3:26])[CH3:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86685857HCID 86685857、化合物

生成物 1

HCID 89599581(NE,S)-2-methyl-N-[2,2,2-trifluoro-1-[4-(6,6,6-trifluorohexoxy)phenyl]ethylidene]propane-2-sulfinamide収率 66%

試薬・触媒・溶媒 4

HCID 178477244HCID 178477244、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回
HCID 8058
Hexane
溶媒
HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of Intermediate 8B (717 mg, 2.184 mmol) and (S)-2-methylpropane-2-sulfinamide (529 mg, 4.37 mmol) in THF (10 mL) was added tetraethoxytitanium (1993 mg, 8.74 mmol) in THF (20 mL). The resulting mixture was reflux for 5 h. TLC (20% EtOAc in hexane) indicated the starting ketone was completely consumed. The solvent was evaporated to afford a yellow oil. This yellow oil was dissolved in EtOAc and then washed with saturated NaHCO3 (25 mL) and a large amount of white precipitation formed which was removed by filtering through a bed of Celite®. The white precipitation was rinsed with EtOAc. The combined EtOAc solution was washed again with saturated NaHCO3, dried (MgSO4) and concentrated. The crude product was purified by silica gel chromatography (40 g silica gel, eluted with EtOAc in hexanes) to afford Intermediate 8C (620 mg, 66%).

後処理

  1. temperatureThe resulting mixture was reflux for 5 h
  2. customwas completely consumed
  3. customThe solvent was evaporated
  4. customto afford a yellow oil
  5. washwashed with saturated NaHCO3 (25 mL)
  6. customa large amount of white precipitation
  7. customformed which
  8. customwas removed
  9. filtrationby filtering through a bed of Celite®
  10. customThe white precipitation
  11. washwas rinsed with EtOAc
  12. washThe combined EtOAc solution was washed again with saturated NaHCO3
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated
  15. customThe crude product was purified by silica gel chromatography (40 g silica gel, eluted with EtOAc in hexanes)

出典と根拠

ORDレコード
ord-8c3c0caf30f04112a83ad239e4f9cce8
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08791091B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート