tert-Butylsulfinamide, (S)-(-)- → HCID 89735588、化合物

HRID 1616231ノート

反応式

HRID 1616231 の反応式
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([Br:12])[CH:5]=1)(=O)[CH3:2].[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C1COCC1.CCOC(C)=O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:12][C:6]1[CH:5]=[C:4](/[C:1](=[N:19]/[S:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])/[CH3:2])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]

参加物

6

反応物 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 133472764-Acetyl-2-bromobenzonitrile

生成物 1

HCID 89735588HCID 89735588、化合物

試薬・触媒・溶媒 3

HCID 11026Titanium isopropoxide触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-acetyl-2-bromobenzonitrile (4.0 g, 18 mmol) and (S)-2-methylpropane-2-sulfinamide (2.4 g, 20 mmol) in THF (35 mL) was added titanium(IV) isopropoxide (8.1 mL, 36 mmol) and the reaction mixture was heated to 40 C under an atmosphere of nitrogen. After 2 hours, the reaction was cooled to room temperature, diluted in EtOAc, washed with saturated sodium bicarbonate, rochelle's salt, brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography gave desired product. MS (M+H)+: observed=327.0/329.0, calculated=327.2/327.2.

後処理

  1. temperaturethe reaction mixture was heated to 40 C under an atmosphere of nitrogen
  2. washwashed with saturated sodium bicarbonate, rochelle's salt, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-ab72164f2db444778f3b9a6e6b4dcbe1
出典データセット
uspto-grants-2014_07
特許番号
US08765784B2

反応ノート

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