Hydrogen Peroxide → 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)-2-fluorobenzamide

HRID 570770ノート

反応式

HRID 570770 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[N:11]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[C:19]([F:26])[CH:18]=3)[C:10]2=S)=[CH:5][C:4]=1[C:28]([F:31])([F:30])[F:29])#[N:2].[OH:32]O>C(O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[N:11]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[C:19]([F:26])[CH:18]=3)[C:10]2=[O:32])=[CH:5][C:4]=1[C:28]([F:31])([F:30])[F:29])#[N:2]

参加物

4

反応物 2

HCID 784Hydrogen PeroxideHCID 70678916N-Desmethylenzalutamide

生成物 1

HCID 468985234-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)-2-fluorobenzamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluorobenzamide (Compound (MII)) (1.48 g, 3.4 mmol) in ethanol (60 mL) was added 30% aqueous H2O2 (30 mL) at room temperature. The solution was heated to reflux for 1 h. After removal of ethanol, brine (100 mL) was added and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product that was purified by silica gel chromatography. MS (m/z): 435 (M+1). HPLC: Column, YMC ODS A, 4.6×150 mm, 5 μm, Mobile Phase A: 10 mM Ammonium acetate, Mobile Phase B: Acetonitrile, Gradient, 10% B up to 2 min, 10% to 90% B in 6 min, hold for 10 min, 90% to 10% B in 4 min, Retention time, 9.548 min, HPLC Purity, 98.08%, Flow Rate, 1 mL/min. 1H NMR (CDCl3, Freebase): δ (ppm) 8.3 (t, 1H), 8.18 (s, 1H), 8.2 (d, 1H), 7.96 (d, 1H), 7.25 (m, 2H), 6.65 (bd, 1H), 5.9 (bs, 1H) 1.65 (s, 6H).

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 h
  3. customAfter removal of ethanol, brine (100 mL)
  4. additionwas added
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ab1b5fab25bb4b3eb93cb4af9df52c67
出典データセット
uspto-grants-2015_05
特許番号
US09023879B2

反応ノート

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