Hydrogen Peroxide → Bicalutamide

HRID 1269472

반응식

HRID 1269472 반응식
[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]

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 962Water2회HCID 11430Potassium CarbonateHCID 9800987Bicalutamide sulfide

생성물 1

HCID 2375Bicalutamide

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

반응 조건

온도
5 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f348955382ac4a4fa025d231d34ea457
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199257B1

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