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p-Toluenesulfonic acid monohydrate → 3-(5-Bromo-2-methylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione

HRID 922134
ノート
印刷プレビュー

反応式

HRID 922134 の反応式
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:36])=[C:18]([C:20]2[C:21](=[O:35])[NH:22][C:23]3([C:33]=2[OH:34])[CH2:32][CH2:31][C:26]2(OCC[O:27]2)[CH2:25][CH2:24]3)[CH:19]=1>CC(C)=O.O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:36])=[C:18]([C:20]2[C:21](=[O:35])[NH:22][C:23]3([CH2:24][CH2:25][C:26](=[O:27])[CH2:31][CH2:32]3)[C:33]=2[OH:34])[CH:19]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 6827112611-(5-Bromo-2-methylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one

生成物 1

HCID 673756183-(5-Bromo-2-methylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回HCID 962Water溶媒2 回

反応条件

温度
80 °C

実験手順

192 mg (1.01 mmol) of 4-toluenesulphonic acid monohydrate were added to 2.49 g (6.32 mmol) of 11-(5-bromo-2-methylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one (Example 38A) in 26 ml of acetone and 13 ml of water. The reaction mixture was stirred at 80° C. overnight. For work-up, the cold reaction mixture was diluted with water and acetone was removed on a rotary evaporator. The precipitated crude product was extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. Drying gave 1.97 g (89% of theory) of the title compound.

後処理

  1. customFor work-up, the cold reaction mixture
  2. customwas removed on a rotary evaporator
  3. customThe precipitated crude product
  4. extractionwas extracted with ethyl acetate
  5. washThe organic phase was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customDrying

出典と根拠

ORDレコード
ord-ac91620567144419936d7f7c1802a9fd
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278925B2

反応ノート

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