Water → Bicalutamide

HRID 1269473

反応式

HRID 1269473 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].[OH2:28].[OH:29]OS([O-])=O.[K+]>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:28])=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2]

参加物

5

反応物 3

HCID 962WaterHCID 9800987Bicalutamide sulfideHCID 23707502Potassium hydroxy sulfite

生成物 1

HCID 2375Bicalutamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

To a solution of 40 g (0.1 mol) of N-[4-cyano-3-trifluoromethyl-phenyl]-3-[4-fluorophenyl-thio]-2-hydroxy-2-methyl-propionamide in 600 ml of methanol and 400 ml of water 100 g (0.16 mol) of Oxone® oxidizing agent [2KHSO5KHSO4K2SO4 salt] was added. The reaction mixture was stirred at 25° C. for 6 h, then the methanol was distilled off under diminished pressure and the residue was extracted twice with 500 ml of dichloromethane. The organic layer was washed twice with 400 ml of 10% aqueous sodium thiosulfate solution, then with 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.

後処理

  1. additionwas added
  2. distillationthe methanol was distilled off under diminished pressure
  3. extractionthe residue was extracted twice with 500 ml of dichloromethane
  4. washThe organic layer was washed twice with 400 ml of 10% aqueous sodium thiosulfate solution
  5. dry with materialwith brine, dried over sodium sulfate
  6. concentrationconcentrated under diminished pressure
  7. 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-fb8594b35111463695d5b9ec3615ff96
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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