Hydrogen Peroxide → Bicalutamide

HRID 1269472

反応式

HRID 1269472 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]([OH:22])([CH3:21])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2].C(=O)([O-])[O-:29].[K+].[K+].OO.[OH2:36]>C(#N)C.CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]([OH:22])([CH3:21])[CH2:12][S:13]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)(=[O:29])=[O:36])=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2]

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 962Water2 回HCID 11430Potassium CarbonateHCID 9800987Bicalutamide sulfide

生成物 1

HCID 2375Bicalutamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
5 °C

実験手順

To a solution of 2 g (2.51 mmol) of N-[4-cyano-3-trifluoromethyl-phenyl]-3-[4-fluorophenyl-thio]-2-hydroxy-2-methyl-propionamide in 10 ml of acetonitrile, 20 ml of methanol and 0.6 ml of water 0.38 g (2.75 mmol) of potassium carbonate was added. The mixture was cooled to 5° C. and 10 ml of 30% aqueous hydrogen peroxide solution was added dropwise. The mixture was stirred at 25° C. overnight, then diluted with 100 ml of water and extracted twice with 100 ml of dichloromethane. The organic layer was washed with 50 ml of brine, dried over sodium sulfate and concentrated under diminished pressure. The residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which has a boiling range of 40–70° C. The yield was 1.53 g (70.83%).

後処理

  1. extractionextracted twice with 100 ml of dichloromethane
  2. washThe organic layer was washed with 50 ml of brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under diminished pressure
  5. customThe residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which

出典と根拠

ORDレコード
ord-f348955382ac4a4fa025d231d34ea457
出典データセット
uspto-grants-2007_04
特許番号
US07199257B1

関連ノート

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